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Method for synthesizing (E)-1-chlorine-6, 6-dimethyl-2-heptylene-4-alkyne

A synthesis method and dimethyl technology, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve the problems of harsh reaction conditions, low product purity, and long synthesis route. , to achieve the effect of simple operation, high yield and few steps

Active Publication Date: 2010-01-13
SHANDONG BOYUAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The above two synthetic routes are long, with many steps and complicated operation; the reaction conditions are harsh (the first step reaction process needs to be strictly anhydrous, nitrogen protection); the product has low purity and low yield (not higher than 70%)

Method used

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  • Method for synthesizing (E)-1-chlorine-6, 6-dimethyl-2-heptylene-4-alkyne
  • Method for synthesizing (E)-1-chlorine-6, 6-dimethyl-2-heptylene-4-alkyne
  • Method for synthesizing (E)-1-chlorine-6, 6-dimethyl-2-heptylene-4-alkyne

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0022] Weigh 111 grams of trans-1,3-dichloropropene, 100 grams of tetrahydrofuran, and 204 grams of tri-n-butylamine, put them into the reaction flask, start stirring, add tetrakis (triphenylphosphine) palladium (0) 5.8 g, 0.96 g of cuprous iodide was added dropwise with 82 g of tert-butylacetylene, the rate of addition was controlled, and the temperature was maintained at 40°C. After the dropwise addition was completed, the reaction was incubated for 30 hours. After the reaction was completed, tetrahydrofuran was distilled off under reduced pressure. Add 200 grams of petroleum ether, stir for 20 minutes, wash three times with 8-12% dilute ammonia by weight, 100ml each time, dry, filter with suction, evaporate petroleum ether under reduced pressure to obtain a crude product.

[0023] Distill the crude product under reduced pressure and collect the fraction at 70-80°C (15mmHg) to obtain (E)-1-chloro-6,6-dimethyl-2-hepten-4-yne as a colorless to pale yellow transparent liquid ...

example 2

[0025] Weigh 111 grams of trans-1,3-dichloropropene, 100 grams of tetrahydrofuran, and 622 grams of tri-n-heptylamine, put them into the reaction flask, start stirring, add bis(triphenylphosphine)palladium(II) chloride 3.5 gram, cuprous iodide 0.96g, all the other are with example 1, obtain (E)-1-chloro-6,6-dimethyl-2-hepten-4-yne 138 grams; Product yield 88.1%.

Embodiment 3

[0027] Weigh 222 grams of trans-1,3-dichloropropene, 180 grams of tetrahydrofuran, and 303 grams of triethylamine, put them into the reaction flask, start stirring, add 5.1 grams of bis(tri-tert-butylphosphine) palladium and cuprous iodide 1.92 g, 164 g of tert-butylacetylene was added dropwise, the rate of addition was controlled, and the temperature was maintained at 40°C. After the dropwise addition was completed, the reaction was incubated for 20 hours. After the reaction was completed, tetrahydrofuran was distilled off under reduced pressure. Add 350 grams of petroleum ether, stir for 20 minutes, wash three times with 8-12% dilute ammonia by weight, 200ml each time, dry, filter with suction, evaporate petroleum ether under reduced pressure to obtain a crude product.

[0028] The crude product was distilled under reduced pressure, and the fraction at 70-80°C (15mmHg) was collected to obtain 270 g of (E)-1-chloro-6,6-dimethyl-2-hepten-4-yne; the product yield was 86.2%.

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Abstract

The invention discloses a method for synthesizing compound (E)-1-chlorine-6, 6-dimethyl-2-heptylene-4-alkyne. The method has the technical scheme that trans-1, 3-dichloropropylene and tertiary butyl ethyne are taken as raw materials which are processed by condensation reaction to synthesize the (E)-1-chlorine-6, 6-dimethyl-2-heptylene-4-alkyne in one step. Compared with the existing synthesis technique, the method has the advantages of fewer steps, high yield, no pollution for the environment, advancement, simple technique, simple and convenient operation, low requirements for equipment and production environment, and good applicability.

Description

technical field [0001] The present invention relates to a compound synthesis method, in particular to a compound (E)-1-chloro-6,6-dimethyl-2-hepten-4-yne synthesis method. Background technique [0002] (E)-1-chloro-6,6-dimethyl-2-hepten-4-yne, the English chemical name is 1-Chloro-6, and the molecular weight of 6-dimethyl-2-hepten-4-yne is 156.65; CAS#: 126764-17-8; the structural formula is: [0003] [0004] (E)-1-chloro-6,6-dimethyl-2-hepten-4-yne is a key intermediate for the synthesis of terbinafine hydrochloride. Terbinafine hydrochloride is an allylamine broad-spectrum antifungal drug, which can specifically interfere with the early biosynthesis of fungal sterols, selectively inhibit the activity of fungal squalene cyclooxygenase, and make the fungal cell membrane formation process The epoxidation reaction of squalene is hindered, and squalene accumulates in cells, thereby achieving the effect of killing or inhibiting fungi. Terbinafine hydrochloride has a large...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C21/22C07C17/266B01J31/30B01J31/24
Inventor 张志强陈贵军
Owner SHANDONG BOYUAN PHARM CO LTD
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