Sodium borohydride → 4-[2-Cyano-2-(4-trifluoromethoxyphenyl)ethyl]benzoic acid methyl ester

HRID 1816182Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([C:23]#[N:24])[C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[BH4-].[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:23]#[N:24])[C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:20])([F:22])[F:21])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of 4-[2-cyano-2-(4-trifluoromethoxyphenyl)vinyl]benzoic acid methyl ester (9.0 g, 25.92 mmol) in THF (50 mL) was stirred and cooled to −20° C. A solution of sodium borohydride in THF (100 mL) was added during 20 minutes. The cooling bath was removed and the mixture was stirred for two hours at room temperature and then kept at 5° C. for 16 hours. Ice (100 g) was added and the mixture was neutralised (pH 4-5) with 1 M hydrochloric acid (50 mL). The resulting mixture was extracted with DCM and washed with brine. The organic phase was dried (MgSO4), purified (Norite A), filtered and evaporated. The residue was dried at 40° C. in vacuo to afford 8.8 g (97%) of 4-[2-cyano-2-(4-trifluoromethoxyphenyl)ethyl]benzoic acid methyl ester.

Workup

customThe cooling bath was removed
waitkept at 5° C. for 16 hours
additionIce (100 g) was added
extractionThe resulting mixture was extracted with DCM
washwashed with brine
dry with materialThe organic phase was dried (MgSO4)
custompurified (Norite A),
filtrationfiltered
customevaporated
customThe residue was dried at 40° C. in vacuo

Sources & evidence

ORD record: ord-f396a276b43d4798b555a2c6bb4de2dc
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881746B2

Reaction notes

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