(Trifluoromethyl)trimethylsilane → HCID 66965827, compound

HRID 1515061Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:27][C:28]([Si](C)(C)C)([F:30])[F:29].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([CH:17]([OH:18])[C:28]([F:30])([F:29])[F:27])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -30 °C

Procedure

To 2-(2,6-dimethylphenyl)-6-formyl-benzoimidazole-1-carboxylic acid tert-butyl ester (565 mg) was added 16 mL of a 0.5 M solution of trifluoromethyltrimethylsilane in THF. When a solution formed the mixture was cooled to −30° C. then a solution of TBAF (1.76 mL of a 1.0M solution in THF) was added dropwise. The mixture was stirred at −30° C. for 45 min then was allowed to warm to 5° C. The mixture was extracted with EtOAc (2×) and the combined organic layers were dried over sodium sulfate. The solvent was removed under reduced pressure and the resulting foam was purified by flash chromatography using 10% EtOAc/methylene chloride as eluent to give 2-(2,6-dimethyl-phenyl)-6-(2,2,2-trifluoro-1-hydroxyethyl)-benzoimidazole-1-carboxylic acid tert-butyl ester as a waxy solid. MS (ESI)m/z 421 (M+H).

Workup

customWhen a solution formed the mixture
temperatureto warm to 5° C
extractionThe mixture was extracted with EtOAc (2×)
dry with materialthe combined organic layers were dried over sodium sulfate
customThe solvent was removed under reduced pressure
customthe resulting foam was purified by flash chromatography

Sources & evidence

ORD record: ord-9d11682ceacf47fa8b9e064e4ae0cfec
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222248B2

Reaction notes

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