Hydrochloric Acid → HCID 22261992, compound
Reaction equation
[F:1][C:2]([F:16])([O:6][C:7]1[CH:11]=[C:10]([C:12](OC)=[O:13])[O:9][N:8]=1)[CH:3]([F:5])[F:4].[BH4-].[Na+].Cl>CO>[F:16][C:2]([F:1])([O:6][C:7]1[CH:11]=[C:10]([CH2:12][OH:13])[O:9][N:8]=1)[CH:3]([F:4])[F:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 3-(1,1,2,2-tetrafluoroethoxy)-5-isoxazole carboxylate (1.975 g, 8.124 mmol) in methanol (30 ml) was added sodium borohydride (0.40 g, 10.6 mmol) by small portions under ice-cooling, and the mixture was stirred overnight at room temperature. To the reaction solution was added dilute hydrochloric acid, the mixture was stirred at room temperature for 1 hr and washed three times with ethyl acetate. The recovered organic layer was dried over anhydrous magnesium sulfate, and passed through silica gel. The solvent was evaporated under reduced pressure to give a crude product of [3-(1,1,2,2-tetrafluoroethoxy)isoxazol-5-yl]methanol as a yellow liquid (1.72 g).
Workup
- temperaturecooling
- stirringthe mixture was stirred at room temperature for 1 hr
- washwashed three times with ethyl acetate
- dry with materialThe recovered organic layer was dried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-3d55bf8d604145c99123d0fcf52035fc
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06982348B2
Reaction notes
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