Ethyl 2-[2-({[4-(trifluoromethyl)phenyl]sulfonyl}oxy)phenyl]cyclopropanecarboxylate → 2-[2-(Hydroxymethyl)cyclopropyl]phenyl 4-(trifluoromethyl)benzenesulfonate

HRID 1795123Notes

Reaction equation

[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]2[CH2:21][CH:20]2[C:22](OCC)=[O:23])(=[O:11])=[O:10])=[CH:5][CH:4]=1>C1COCC1>[F:27][C:2]([F:1])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]2[CH2:21][CH:20]2[CH2:22][OH:23])(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of ethyl 2-[2-({[4-(trifluoromethyl)phenyl]sulfonyl}oxy)phenyl]-cyclopropanecarboxylate (0.84 g, 2.0 mmol) in THF (2 mL) is treated under an inert atmosphere with a 2 M solution of borane-methyl sulfide complex in THF (1 mL). The reaction is heated to 70° C. for 1 h, and stirred at room temperature overnight. The reaction is worked up by partitioning between ethyl acetate and 1 N HCl. The organic layer is dried and evaporated. The product, 2-[2-(hydroxymethyl)cyclopropyl]phenyl 4-(trifluoromethyl)benzenesulfonate, is obtained as a mixture of isomers. A yield of 93% is obtained.

Workup

customby partitioning between ethyl acetate and 1 N HCl
customThe organic layer is dried
customevaporated

Sources & evidence

ORD record: ord-b0c68f7e7f9e421ea4c554f21495e9a7
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026339B2

Reaction notes

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