Methanol → 5-(Trifluoromethyl)-3-thiophenemethanol
Reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[S:7][CH:6]=[C:5]([C:8](OC)=[O:9])[CH:4]=1.CO.[BH4-].[Na+]>C1COCC1>[F:12][C:2]([F:1])([F:13])[C:3]1[S:7][CH:6]=[C:5]([CH2:8][OH:9])[CH:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of methyl 5-(trifluoromethyl)thiophene-3-carboxylate (523 mg) in THF (1 ml)-MeOH (1 ml) was added NaBH4 (2.2 g) at room temperature, and the reaction mixture was stirred at 60° C. for 3 h. The reaction mixture was quenched with water, and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated and purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (449 mg) as a pale yellow oil.
Workup
- customThe reaction mixture was quenched with water
- extractionextracted with EtOAc
- washThe extract was washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
- custompurified by silica gel column chromatography (hexane/EtOAc)
Sources & evidence
- ORD record
- ord-1e2c80422bdb4179887d3c9cdb8d9899
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365540B2
Reaction notes
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