Dimethylformamide → HCID 86658986, compound
Reaction equation
C[CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1.[H-].[Na+].F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=1[C:21]([F:24])([F:23])[F:22].[CH3:25]N(C)C=O>>[CH3:25][C:5]1([CH2:8][O:9][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=2[C:21]([F:24])([F:23])[F:22])[CH2:4][CH2:3][CH2:2][CH2:7][CH2:6]1Participants
Procedure
30 ml of dried dimethylformamide containing 4-methyl-1-cyclohexanemethanol (1 g, 7.8 mmol) was added to sodium hydride (342.2 mg, 8.58 mmol, 60% dispersed oil) and slowly stirred at room temperature under nitrogen. The mixture was further stirred at room temperature for 30 minutes and added to 5 ml of dried dimethylformamide containing 4-fluoro-3-(trifluoromethyl)benzaldehyde (1.2 g, 7.8 mmol) over 10 minutes. Then, the reaction mixture was stirred at room temperature for 18 hours until the initial product disappeared. 20 ml of ice water was added thereto, and the resulting mixture was extracted with ethyl acetate and water. The organic layer was washed with water several times, dried with anhydrous magnesium sulfate, filtered and solvent-evaporated. The residual oil was chromatographed on the silica gel column (hexane:ethyl acetate=20:1) to afford 4-((methylcyclohexyl)methoxy)-3-(trifluoromethyl)benzaldehyde (1.64 g, yield: 87%).
Workup
- stirringThe mixture was further stirred at room temperature for 30 minutes
- extractionthe resulting mixture was extracted with ethyl acetate and water
- washThe organic layer was washed with water several times
- dry with materialdried with anhydrous magnesium sulfate
- filtrationfiltered
- customsolvent-evaporated
- customThe residual oil was chromatographed on the silica gel column (hexane:ethyl acetate=20:1)
Sources & evidence
- ORD record
- ord-62369728412e462e9ea3bc71b4a15b9d
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637558B2
Reaction notes
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