Bromomethylcyclopropane → methyl (S)-3-(4-bromophenyl)-2-(cyclopropylmethoxy)propanoate

HRID 1009221Notes

Reaction equation

Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C@H:14]([OH:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1>C(OCC)C.[Ag]=O>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C@H:14]([O:19][CH2:2][CH:3]2[CH2:5][CH2:4]2)[C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 50 °C

Procedure

0.11 ml (1.15 mmol) of bromomethylcyclopropane are added to a mixture of 267 mg (3.48 mmol) of silver oxide and 100 mg (0.38 mmol) of methyl (S)-3-(4-bromophenyl)-2-hydroxypropionate in 2 ml of diethyl ether. The reaction mixture is stirred at 50° C. for 24 hours. The mixture is filtered and then the solvents are evaporated. The residue is chromatographed on silica gel (heptane/ethyl acetate 85/15). 145 mg of methyl (S)-3-(4-bromophenyl)-2-(cyclopropylmethoxy)propanoate are obtained in the form of an oil. Yield=50%.

Workup

filtrationThe mixture is filtered
customthe solvents are evaporated
customThe residue is chromatographed on silica gel (heptane/ethyl acetate 85/15)

Sources & evidence

ORD record: ord-fd2c854467f043b0beeddc518a933bcf
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973063B2

Reaction notes

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