Ethyl acetate hexane → 2-[(1R,2S)-2-(4-Bromophenyl)cycloprop-1-yl]ethanol

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@@H:9]2[CH:11]=[CH2:12])=[CH:4][CH:3]=1.CCCCCC.C(OCC)(=[O:21])C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@@H:9]2[CH2:11][CH2:12][OH:21])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 21226206Ethyl acetate hexane

HCID 684062521-Bromo-4-[(1S,2R)-2-vinylcyclopropyl]benzene

Product 1

HCID 684071222-[(1R,2S)-2-(4-Bromophenyl)cycloprop-1-yl]ethanol

Procedure

The product from Example 30B was subjected to the conditions outlined in Example 26F, followed by chromatography (7:3 hexane/ethyl acetate) to provide the title compound.

Sources & evidence

ORD record: ord-ed5d1466003f4bdbb4ba42bf36fe4782
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108948B2

Reaction notes

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