Ethanol → alpha5,alpha5-Dimethyl-3,5-isoxazoledimethanol
Reaction equation
[OH:1][C:2]([C:5]1(C(OCC)=O)[O:9][NH:8][CH:7]=[CH:6]1)([CH3:4])[CH3:3].[BH4-].[Na+].O.[CH2:18]([OH:20])C>>[OH:1][C:2]([C:5]1[O:9][N:8]=[C:7]([CH2:18][OH:20])[CH:6]=1)([CH3:3])[CH3:4]Participants
5
Procedure
9.96 g of ethyl 5-(1-hydroxy-1-methylethyl)isoxazole-5-carboxylate was dissolved in 200 ml of ethanol, and 3.78 g of sodium borohydride was then added. The mixture was stirred at room temperature for 10 hours. After 50 ml of water was added, the reaction mixture was concentrated to 50 ml under reduced pressure. The concentrated solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced-pressure. The residue was subjected to silica gel column chromatography to obtain 6.17 g of [5-(1-hydroxy-1-methylethyl)isoxazol-3-yl]methanol.
Workup
- concentrationthe reaction mixture was concentrated to 50 ml under reduced pressure
- extractionThe concentrated solution was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced-pressure
Sources & evidence
- ORD record
- ord-db71d2d1758943638f0d40741394bb0b
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846956B2
Reaction notes
Loading…