Water → Methyl alpha-(2-methoxymethylphenyl)-beta-methylacrylate

HRID 1656705

Reaction equation

[C:1]([O-])(C)(C)[CH3:2].[K+].[CH3:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=O)[C:17]([O:19][CH3:20])=[O:18].O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.O1CCCC1>[CH3:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=[CH:1][CH3:2])[C:17]([O:19][CH3:20])=[O:18]

Participants

Conditions

Temperature: 5 °C

Procedure

37.1 g (100 mmol) of ethyltriphenylphosphonium bromide are introduced under nitrogen into 300 ml of absolute tetrahydrofuran. At 5° C., 11.2 g (0.1 mol) of potassium t-butanolate are added. After stirring at 5° C. for one hour, 20.8 g (100 mmol) of methyl 2-methoxymethylphenylglyoxylate in 100 ml of tetrahydrofuran are added dropwise. The mixture is stirred at 5° C. for one hour and at 25° C. for one hour, 200 ml of water are added, the mixture is extracted with methylene chloride and the organic phases are washed with water. After drying over sodium sulfate, the solvent is removed under reduced pressure. The residue is purified by chromatography on a silica gel column (methyl tert-butyl ether/n-hexane=1/2). 17.2 g (78%) of the abovementioned ester are obtained as an oil (Z/E isomer=1/9).

Workup

stirringThe mixture is stirred at 5° C. for one hour and at 25° C. for one hour
extractionthe mixture is extracted with methylene chloride
washthe organic phases are washed with water
dry with materialAfter drying over sodium sulfate
customthe solvent is removed under reduced pressure
customThe residue is purified by chromatography on a silica gel column (methyl tert-butyl ether/n-hexane=1/2)

Sources & evidence

ORD record: ord-430c73b53cba4c019b60cda228d80024
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254717

Linked notes

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