Sodium borohydride → [2-(Difluoromethyl)-1,3-thiazol-4-yl]methanol
Reaction equation
[F:1][CH:2]([F:13])[C:3]1[S:4][CH:5]=[C:6]([C:8](OCC)=[O:9])[N:7]=1.[BH4-].[Na+]>CO>[F:1][CH:2]([F:13])[C:3]1[S:4][CH:5]=[C:6]([CH2:8][OH:9])[N:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of ethyl 2-(difluoromethyl)thiazole-4-carboxylate (100 mg) in MeOH (1 ml) was added NaBH4 (36.5 mg) at 0° C., and the mixture was stirred at 0° C. for 3 h. The mixture was quenched with saturated NH4Cl solution, and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (44.0 mg) as a pale yellow oil.
Workup
- customThe mixture was quenched with saturated NH4Cl solution
- extractionextracted with EtOAc
- customThe organic layer was separated
- washwashed with water and brine successively
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc)
Sources & evidence
- ORD record
- ord-a88d85b481a546f38eaf70549a923a48
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365540B2
Reaction notes
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