Unlock instant, AI-driven research and patent intelligence for your innovation.
3-Acetyl-10,11-dihydro-5h-dibenzo[c,g]chromene-8(9h)-one synthesis process
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
A synthesis process, acetyl technology, applied to 3-acetyl-10, can solve the problems of high cost, low product yield, difficult purification, etc., and achieve the effect of improving product quality, reducing cost, and reducing three wastes
Active Publication Date: 2020-05-26
SULI PHARMA TECH JIANGYIN
View PDF2 Cites 0 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
Problems solved by technology
[0014] The present invention aims to provide a synthesis process of 3-acetyl-10,11-dihydro-5H-dibenzo[C,G]chromene-8(9H)-one, which solves the problem of preparing 3-acetyl-10 in the past. , The cost of 11-dihydro-5H-dibenzo[C,G]chromen-8(9H)-one is high (catalyst is one of the main cost sources), the product yield is not high, and purification is difficult, etc.
Method used
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
Examples
Experimental program
Comparison scheme
Effect test
Embodiment 1
[0055] Steps: (1): Preparation of 1-(4-bromo-3-(((3,4-dihydro-2H-spiro[1,2'-[1,3]dioxolane]-7-naphthyl )oxy)methyl)phenyl)ethanone
Synthetic example 1
[0057] Add 29.1g (0.179mol) 7-hydroxy-3,4-dihydro-2H-1-naphthone, 100mL ethylene glycol, 25.3g (0.238mol) trimethyl Oxymethane and 2.91 g (10 wt %) of n-butylammonium tribromide. After the addition, continue to stir at room temperature for 1 hour, add 28.4g (0.206mol) of potassium carbonate, 50g (0.171mol) of 1-(4-bromo-3-(bromomethyl)phenyl)ethane-1- Ketone and 100mL ethanol were heated to 50°C for 3h. The reaction was cooled to 25° C., water and ethyl acetate were added in sequence, the liquid was separated, and the organic phase was concentrated to obtain 69.6 g of white solid, with a yield of 93.2%. 1HNMR (DMSO-d6, 400MHz) δppm8.14 (s, 1H), 7.85-7.86 (d, 2H), 7.04-7.07 (d, 1H), 7.00-7.01 (d, 1H), 6.95-6.97 (d, 1H), 5.17 (s, 2H), 4.01-4.11 (m, 4H), 2.65-2.68 (t, 2H), 2.59 (s, 3H), 1.81-1.83 (m, 4H).
Synthetic example 2
[0059] Add 29.1g (0.179mol) 7-hydroxy-3,4-dihydro-2H-1-naphthone, 100mL ethylene glycol, 25.3g (0.238mol) trimethyl Oxymethane and 2.91 g (10 wt %) of pyridinium tribromide. After the addition, continue to stir at room temperature for 1 hour, add 28.4g (0.206mol) of potassium carbonate, 50g (0.171mol) of 1-(4-bromo-3-(bromomethyl)phenyl)ethane-1- Ketone and 100mL ethanol were heated to 50°C for 3h. The reaction was cooled to 25° C., water and ethyl acetate were added in sequence, the liquid was separated, and the organic phase was concentrated to obtain 68.3 g of white solid (71.3 g in theoretical amount), with a yield of 91.5%. 1HNMR (DMSO-d6, 400MHz) δppm8.14 (s, 1H), 7.85-7.86 (d, 2H), 7.04-7.07 (d, 1H), 7.00-7.01 (d, 1H), 6.95-6.97 (d, 1H), 5.17 (s, 2H), 4.01-4.11 (m, 4H), 2.65-2.68 (t, 2H), 2.59 (s, 3H), 1.81-1.83 (m, 4H).
[0060] Step (2): Preparation of 1-(10,11-dihydro-5H,9H-spiro[dibenzo[C,G]chromene-8,2'-[1,3]dioxolane]-3 -Synthetic example 1 of ethyl) ethyl ket...
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
PUM
Login to View More
Abstract
The invention provides a synthesis process of 3-acetyl-10,11-dihydro-5H-dibenzo[C,G]chromene-8(9H)-one. The synthesis process does not use allyltrimethylsilane, and is characterized in that raw materials undergo ketone protection, raw materials demanded in a next step are synthesized through a one-pot method, and the product can be prepared through three steps of reaction. The synthesis process has the following advantages that protection of the ketone helps increase activity of a reactant, improve the reaction yield, reduce the use amount of a palladium catalyst, greatly lower the cost, simplify the purification process and improve the product quality.
Description
technical field [0001] The invention relates to a synthesis process of 3-acetyl-10,11-dihydro-5H-dibenzo[C,G]chromene-8(9H)-one, in particular to a method for protecting ketones to achieve A new process for improving product yield and purity and reducing costs. Background technique [0002] 3-Acetyl-10,11-dihydro-5H-dibenzo[C,G]chromen-8(9H)-one is an important intermediate used as an antiviral drug to treat hepatitis C. At present, its synthesis method has the following two kinds: [0003] Method 1: 4-bromo-2-(bromomethyl)-1-chlorobenzene and 7-hydroxy-3,4-dihydro-2H-1-naphthalenone are used as raw materials in the patent application with the application number WO2013 / 75029 The following reaction formula was used to prepare 3-acetyl-10,11-dihydro-5H-dibenzo[C,G]chromen-8(9H)-one. [0004] [0005] Its disadvantages are as follows: [0006] 1) The boiling point of trimethylacetylene is low, and the selection of factory production reactors has great limitations, which ...
Claims
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
![3-Acetyl-10,11-dihydro-5h-dibenzo[c,g]chromene-8(9h)-one synthesis process](https://images-eureka.patsnap.com/patent_img/282ac13d-236e-4334-b77d-70d4daeb9aa8/181008135428.png)
![3-Acetyl-10,11-dihydro-5h-dibenzo[c,g]chromene-8(9h)-one synthesis process](https://images-eureka.patsnap.com/patent_img/282ac13d-236e-4334-b77d-70d4daeb9aa8/BDA0001822463660000011.png)
![3-Acetyl-10,11-dihydro-5h-dibenzo[c,g]chromene-8(9h)-one synthesis process](https://images-eureka.patsnap.com/patent_img/282ac13d-236e-4334-b77d-70d4daeb9aa8/BDA0001822463660000021.png)
Login to View More 
Login to View More