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

HRID 1801622Notes

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-387fcde0bdf34bf8a7a02c1a1f09e9be
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349843B2

Reaction notes

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