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Preparation of homoallylic alcohols

A technology of homoallyl alcohol and allyl halide, applied in the preparation of hydroxyl compounds, organic compounds, chemical instruments and methods, etc., can solve the problems of large amount of raw materials and solvents, complex reaction system, and high cost of reagents, etc. Achieve the effects of simplification of the reaction system, easy availability of raw materials, and reduction of the amount of raw materials

Inactive Publication Date: 2009-07-08
NORTHWEST NORMAL UNIVERSITY
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  • Description
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AI Technical Summary

Problems solved by technology

In 2002, Wang et al. reported that gallium promotes the allylation reaction of aldehyde ketone and allyl bromide in aqueous phase. Although the yield of this method is high, the reaction time is long, and the reaction must be carried out under heating ( Tetrahedron Letters, 200243, 5097)
In 2004, Chan et al. reported the allylation reaction of aromatic aldehydes with allyl bromide and allyl chloride in aqueous phase under the promotion of metal iron. The yield of this method is good, but the reaction time is as long as 144 hours, and the reaction is in progress. Need to add sodium fluoride as an auxiliary reagent (Tetrahedron Letters, 2004, 45, 4189)
(1) Large amount of raw materials and solvents; (2) Need to add catalyst; (3) Long reaction time; (4) High cost of reagents; (5) Complex reaction system

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1 A kind of preparation method of homoallyl alcohol, comprises the following steps:

[0024] (1) Put metal indium, n-butyraldehyde, allyl bromide, and 1,2-dibromoethane into the reaction solvent tetrahydrofuran in turn, and react at a temperature of 25°C. The whole reaction process is tracked by thin-layer chromatography , that is to take samples every 5 minutes, use a capillary tube to drip the reaction solution and the raw material n-butyraldehyde onto the silica gel plate respectively. The two spots are on the same straight line, and then put the silica gel plate into It is a 20:1 mixture of petroleum ether and ethyl acetate in an exhibition bottle. After the plate transfer is completed, put the silica gel plate under an ultraviolet lamp or in an iodine bottle for observation. If there is no point flush with the n-butyraldehyde of the raw material solution in the reaction solution, it indicates that the reaction is complete, and the reaction solution is ob...

Embodiment 2

[0029] Embodiment 2 A kind of preparation method of homoallyl alcohol is the same as embodiment 1.

[0030] The aldehyde and ketone compound is benzaldehyde, the allyl halide is allyl bromide, the activator is trimethylbromosilane, and the reaction solvent is tetrahydropyran.

[0031] The molar ratio of metal indium to benzaldehyde is 1:1.0, the molar ratio of metal indium to allyl bromide is 1:1.8, the molar ratio of metal indium to trimethylbromosilane is 1:1.2, and the molar ratio of metal indium to tetrahydropyridine The molar ratio of Nan is 1:15.

[0032] The reaction temperature was 40°C, the time was 2.0 h, and the yield was 62.1%.

Embodiment 3

[0033] Example 3 A preparation method of homoallyl alcohol is the same as Example 1.

[0034] The aldehyde and ketone compound is p-chlorobenzaldehyde, the allyl halide is allyl chloride, the activator is trimethylchlorosilane, and the reaction solvent is ether.

[0035] The molar ratio of metal indium to p-chlorobenzaldehyde is 1:0.8, the molar ratio of metal indium to allyl chloride is 1:2.0, the molar ratio of metal indium to trimethylchlorosilane is 1:1.5, and the molar ratio of metal indium to diethyl ether The molar ratio is 1:10.

[0036] The reaction temperature was 20°C, the time was 1.5 h, and the yield was 90.2%.

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Abstract

The invention relates to a method for preparing high-allyl alcohol. The method comprises the steps of taking metallic indium as an accelerator, taking saturated dihalide and silane as activators and forming high-allyl alcohol through the reaction of aldehyde ketone compounds and allyl halide at a temperature between 10 and 50 DEG C. The method has the advantages of mild reaction conditions, simple post-treatment, high product yield, no need for operation with no water or oxygen, capability of realizing large-scale production and good industrial application prospects.

Description

technical field [0001] The invention relates to homoallyl alcohol in the field of organic synthetic chemistry, in particular to a preparation method of homoallyl alcohol. Background technique [0002] Homoallyl alcohol, as an important class of organic synthesis intermediates, has important uses in the synthesis of medicine, pesticides and natural products. An important method for the synthesis of homoallylic alcohols is the metal-promoted allylation of aldehydes and ketones with allyl halides. In 2002, Wang et al. reported that gallium promotes the allylation reaction of aldehyde ketone and allyl bromide in aqueous phase. Although the yield of this method is high, the reaction time is long, and the reaction must be carried out under heating ( Tetrahedron Letters, 200243, 5097). In 2004, Chan et al. reported the allylation reaction of aromatic aldehydes with allyl bromide and allyl chloride in aqueous phase under the promotion of metal iron. The yield of this method is goo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/03C07C29/38
Inventor 杜正银李艳春
Owner NORTHWEST NORMAL UNIVERSITY
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