Water → [2-(Dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)phenyl]methanol
Reaction equation
[BH4-].[Na+].[CH3:3][O:4][CH:5]([O:22][CH3:23])[C:6]1[C:13]([O:14][CH2:15][O:16][CH3:17])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9].O>O1CCCC1CO>[CH3:23][O:22][CH:5]([O:4][CH3:3])[C:6]1[C:13]([O:14][CH2:15][O:16][CH3:17])=[C:12]([C:18]([F:19])([F:20])[F:21])[CH:11]=[CH:10][C:7]=1[CH2:8][OH:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium borohydride (5.11 g, 135 mmol) was added to a solution of crude 2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzaldehyde obtained in Example (6-5) in a mixture of tetrahydrofuran-methanol (5:1, 100 ml) under ice-cooling and the mixture was stirred overnight. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate (four times), the organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the sol-vent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1-2/1) to give [2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)phenyl]methanol as an orange oil (22.6 g, two-step total yield: 52%).
Workup
- temperaturecooling
- extractionthe mixture was extracted with ethyl acetate (four times)
- washthe organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution
- dry with materialdried with anhydrous sodium sulfate
- customThe residue obtained
- customby removing the sol-vent under reduced pressure
- customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1-2/1)
Sources & evidence
- ORD record
- ord-d7ca66b528c446aa8aa4087b9e38de6a
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07923573B2
Reaction notes
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