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MBH reaction of alpha, beta-unsaturated ketone and allyl acetate

An allyl acetate, unsaturated technology, applied in the separation/purification of carbonyl compounds, preparation of carbonyl compounds, chemical instruments and methods, etc., to achieve the effects of high yield, easier preparation, and mild reaction conditions

Inactive Publication Date: 2016-05-04
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the MBH alkylation reaction between α,β-unsaturated compounds and allyl esters or allyl alcohol molecules has not been reported yet.

Method used

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  • MBH reaction of alpha, beta-unsaturated ketone and allyl acetate
  • MBH reaction of alpha, beta-unsaturated ketone and allyl acetate
  • MBH reaction of alpha, beta-unsaturated ketone and allyl acetate

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Embodiment 1

[0028] Embodiment 1, utilize α, the MBH reaction method of β-unsaturated ketone and allyl acetate, carry out following steps successively:

[0029] 1), in α, β-unsaturated ketone (0.1mmol) and acetic acid (12.0mg, 0.2mmol) in 1,4-dioxane solution (2mL), add tributylphosphine P (n-Bu) 3 (20.2 mg, 0.1 mmol). After the mixture was stirred for 1 minute, Pd(PPh 3 ) 4 (11.6 mg, 0.01 mmol) and allyl acetate (0.3 mmol). The mixture was stirred and reacted at 60° C. for 24 hours.

[0030] The α,β-unsaturated ketone is in particular 1a p-methylphenyl vinyl ketone;

[0031] Allyl acetate is specifically 2a allyl acetate;

[0032] 2), the reaction product obtained in step 1) was rotary evaporated to remove the solvent (i.e., 1,4-dioxane), and the residue was purified by column chromatography, using 200-300 mesh silica gel, and ethyl acetate:petroleum ether =1:100 (volume ratio) as eluent, and the obtained eluate was rotary evaporated to obtain 2-methylene-1-(p-tolyl)pent-4-en-1-one(...

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Abstract

The invention discloses an MBH reaction of alpha, beta-unsaturated ketone and allyl acetate. The reaction comprises the following steps that 1, alpha, beta-unsaturated ketone, acetic acid and a catalyst are added into solvent and stirred, then Pd(PPh3)4 and allyl acetate are added, and the mixture reacts for 22-26 hours in a stirred mode at the temperature of 50 DEG C-70 DEG C; 2, a reaction product obtained in the step 1 is decompressed, the solvent is steamed away, and residues are subjected to column chromatography separation to obtain alpha-allyl substituted alpha, beta-unsaturated ketone. Adopted allyl acetate is easier to prepare, and alpha, beta-unsaturated ketone with the open chain is used. Because acetic acid is added, alpha, beta-unsaturated ketone is prevented from generating the MBH reaction by itself.

Description

technical field [0001] The present invention relates to the MBH reaction of α,β-unsaturated ketones with allyl acetate. Background technique [0002] The Morita-Baylis-Hillman (MBH) reaction is an important synthetic reaction for the formation of carbon-carbon bonds. The reaction atom is economical and can form multifunctional compounds, which are widely used in organic synthesis and drug synthesis. Although α,β-unsaturated compounds can successfully undergo MBH reactions with electrophiles such as aldehydes, 1,2-diketones, and imines, the alkylation of MBH is still challenging. It has been reported in the literature that cyclic α,β-unsaturated ketones can undergo MBH alkylation reactions with allyl halides. Compared with allyl halides, allyl alcohols and their esters are generally easier to prepare. However, the MBH alkylation reaction between α,β-unsaturated compounds and allyl esters or allyl alcohol molecules has not been reported so far. Contents of the invention ...

Claims

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Application Information

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IPC IPC(8): C07C45/70C07C45/78C07C49/794C07C49/84C07C49/807C07C49/80C07C49/796C07C49/813C07C205/45C07C201/12
CPCC07C45/70C07C45/78C07C201/12C07C49/794C07C49/84C07C49/807C07C49/80C07C49/796C07C49/813C07C205/45
Inventor 黄志真李娅琼王海君何牮石
Owner ZHEJIANG UNIV
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