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Synthetic method of aliphatic pinacol

A synthesis method and technology of pinacol, applied in chemical instruments and methods, preparation of hydroxy compounds, preparation of organic compounds, etc., can solve the problems of complicated operation process, harsh reaction conditions, few reports of pinacol coupling reaction, etc., Achieve the effect of good chemical selectivity, efficient synthesis method and good application value

Active Publication Date: 2022-08-02
GUANGDONG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

One of the classic and effective methods for synthesizing pinacol is the reductive coupling of carbonyl compounds, which is usually realized by the action of carbonyl compounds and corresponding metal reagents or metal complexes. The coupling product has two chiral centers, which is pinacol. Efficient synthesis of alcohols adds to the difficulty
[0003] Classical synthetic methods often have long reaction time, harsh reaction conditions, complicated operation process, and some yields are relatively low
Moreover, most reaction systems are only suitable for aromatic substrates, and there are few reports on the pinacol coupling reaction of aliphatic aldehydes and ketones.
Aliphatic aldehydes and ketones are relatively difficult to reduce, and their carbonyl radical intermediates are very unstable, so there are few reports for pinacol coupling reactions

Method used

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  • Synthetic method of aliphatic pinacol
  • Synthetic method of aliphatic pinacol
  • Synthetic method of aliphatic pinacol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Synthesis of 6,7-dimethyldodecane-6,7-diol (2a)

[0026]

[0027] Under nitrogen atmosphere, diheptanone 1a (114.0 mg, 1 mmol), samarium metal powder (115 mg, 1 mmol), trimethylsilyl bromide (TMSBr, 132 μL, 1 mmol), tetrahydrofuran (THF) were successively added to a 10 mL dry two-necked flask. , 3 mL), and reacted at room temperature for 0.5 hours. After the reaction, an excess of tetrabutylammonium fluoride solution in tetrahydrofuran was added and stirred for one hour, and then ether was used as the extractant to extract three times (20 mL*3). After the extraction, the organic phases were combined and the solvent was removed using a rotary evaporator. A concentrated crude product was obtained.

[0028] The crude product is separated by a sand-plate chromatography column, and the selected developing agent is petroleum ether and ethyl acetate, and the volume ratio is 8:1 to obtain the product 6,7-dimethyldodecane-6, 7-Diol, 78% yield, oily liquid; see fi...

Embodiment 2

[0029] Example 2 Synthesis of 2,3-dicyclohexylbutane-2,3-diol (2b)

[0030]

[0031] Under a nitrogen atmosphere, acetylcyclohexane 1b (126.0 mg, 1 mmol), samarium metal powder (115 mg, 1 mmol), trimethylsilyl bromide (TMSBr, 132 μL, 1 mmol), tetrahydrofuran were successively added to a 10 mL dry two-necked flask. (THF, 3 mL) and reacted at room temperature for 0.5 hours. After the reaction, an excess of tetrabutylammonium fluoride solution in tetrahydrofuran was added and stirred for one hour, and then ether was used as the extractant to extract three times (20 mL*3). After the extraction, the organic phases were combined and the solvent was removed using a rotary evaporator. A concentrated crude product was obtained.

[0032] The crude product was separated by a sand plate chromatography column, and the selected developing solvent was petroleum ether and ethyl acetate, with a volume ratio of 8:1 to obtain the product 2,3-dicyclohexylbutane-2,3 -Diol, 78% yield, white so...

Embodiment 3

[0033] Example 3 Synthesis of 2,2,5,5-tetramethylhexane-3,4-diol (2c)

[0034]

[0035] Under a nitrogen atmosphere, pivalaldehyde 1c (86.0 mg, 1 mmol), samarium metal powder (115 mg, 1 mmol), trimethylsilyl bromide (TMSBr, 132 μL, 1 mmol), tetrahydrofuran (THF) were successively added to a 10 mL dry two-necked flask. , 3 mL), and reacted at room temperature for 0.5 hours. After the reaction, add excess tetrabutylammonium fluoride solution in tetrahydrofuran, stir for one hour, and then use diethyl ether as the extractant to extract three times (20mL*3). After the extraction, combine the organic phases and use a rotary evaporator to remove the solvent to obtain Concentrated crude product.

[0036] The crude product was separated by a sand plate chromatography column by column chromatography, and the selected developing solvent was petroleum ether and ethyl acetate in a volume ratio of 8:1. The product 2,2,5,5-tetramethylhexane-3,4-diol was obtained, yield 48%, white solid...

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Abstract

The invention provides a method for synthesizing aliphatic pinacol. The reaction conditions are mild, the reaction yield is high and the reaction time is short. Interaction, reductive coupling of substrates, and rapid construction of a variety of aliphatic pinacols.

Description

technical field [0001] The invention relates to a method for synthesizing pinacol, in particular to a method for synthesizing aliphatic pinacol, and belongs to the technical field of organic synthesis. Background technique [0002] Pinacol coupling reaction is one of the most effective methods to construct carbon-carbon single bonds, and it is a hot research field in organic synthesis at present. Its product, pinacol, is an important intermediate in organic synthesis. It has two chiral centers. After splitting, it can be used as a chiral reagent for asymmetric synthesis or used to construct biologically active skeleton molecules. It is widely used in natural products. and the synthesis of pharmaceutical intermediates. One of the classic and effective methods for the synthesis of pinacol is the reductive coupling of carbonyl compounds, which is usually achieved by the interaction of carbonyl compounds with corresponding metal reagents or metal complexes. The coupling product...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/38C07C29/86C07C29/88C07C31/20C07C31/27
CPCC07C29/38C07C29/86C07C29/88C07C2601/14C07C31/20C07C31/27
Inventor 方岩雄王欣灿王小霞
Owner GUANGDONG UNIV OF TECH
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