Sodium borohydride → 3-(4-(3-(Trifluoromethyl)phenoxy)phenyl)propanenitrile
Reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]#[N:16])=[CH:9][CH:8]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]([F:20])([F:21])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][C:15]#[N:16])=[CH:11][CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 3-(4-(3-(trifluoromethyl)phenoxy)phenyl)acrylonitrile (5 g, 17.29 mmol) in Ethanol (80 mL) was added NaBH4 (4.5 g, 119 mmol). The reaction mixture was stirred at 70° C. overnight. After cooling to room temperature, the reaction mixture was quenched with water (50 mL), and ethanol was removed under reduced pressure. The residue was partitioned between EA (100 mL) and water (50 mL). The organic phase was washed with saturated NaHCO3 solution (80 mL), brine (50 mL), dried over sodium sulfate, concentrated, and purified via flash chromatography to afford the title compound (4.3 g, 13.89 mmol, 80% yield) as colorless oil. LCMS: rt=1.64 min, no MS signal
Workup
- temperatureAfter cooling to room temperature
- customthe reaction mixture was quenched with water (50 mL), and ethanol
- customwas removed under reduced pressure
- customThe residue was partitioned between EA (100 mL) and water (50 mL)
- washThe organic phase was washed with saturated NaHCO3 solution (80 mL), brine (50 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- custompurified via flash chromatography
Sources & evidence
- ORD record
- ord-079c2862470441a8a178923bbb4fea6e
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174968B2
Reaction notes
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