Methyl 3,3-diphenyloxirane-2-carboxylate → Methyl 2-hydroxy-3,3-diphenylbutyrate

HRID 251406Notes

Reaction equation

[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:13][CH:8]2[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cu][C:21]#N.C[Li]>CCOCC.O>[OH:13][CH:8]([C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:21])[C:9]([O:11][CH3:12])=[O:10]

Participants

Conditions

Temperature: -78 °C

Procedure

1.5 g (5.9 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate dissolved in 10 ml of absolute ether were added dropwise to a cup-rate solution which had been prepared from 635 mg (7 mmol) of copper(I) cyanide dissolved in 10 ml of absolute ether and 8.14 ml (13 mmol) of a 1.6 normal methyllithium solution and had been cooled to −78° C. The solution was stirred at −78° C. for 1 h and then allowed to warm to room temperature. It was subsequently diluted with 100 ml of ether and 100 ml of water, and the ether phase was washed with dilute citric acid and with sodium bicarbonate solution and dried over magnesium sulfate. The crude product was purified by chromatography on silica gel with cyclohexane/ethyl acetate mixtures to result in 250 mg (16%) of a pale yellow oil.

Workup

additionwere added dropwise to a cup-rate solution which
temperatureto warm to room temperature
washthe ether phase was washed with dilute citric acid and with sodium bicarbonate solution
dry with materialdried over magnesium sulfate
customThe crude product was purified by chromatography on silica gel with cyclohexane/ethyl acetate

Sources & evidence

ORD record: ord-6961d1c367824e28a6c271aaa7e7c812
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863445B2

Reaction notes

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