Ethyl Acetate → 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3-methyl-1-butanol
Reaction equation
[CH3:1][CH:2]([CH3:14])[CH:3]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])[CH:4]=[O:5].[BH4-].[Na+].C(OCC)(=O)C>C1COCC1.C(O)C>[CH3:1][CH:2]([CH3:14])[CH:3]([O:6][Si:7]([C:10]([CH3:11])([CH3:13])[CH3:12])([CH3:8])[CH3:9])[CH2:4][OH:5]Participants
6
Procedure
A stirred, ice-cooled solution of 3-methyl-2-(tert-butyldimethylsilyloxy)butanal (Preparation 7) (0.5 g) in THF (4 ml) and ethanol (8 ml) was treated with sodium borohydride (0.1 g). After 20 minutes, the reaction mixture was worked-up (ethyl acetate) to give the intermediate 3-methyl-2-(tert-butyldimethylsilyloxy)-1-butanol as an oil. This was dissolved in dichloromethane (5 ml), cooled to 0° C., and treated with pyridine (0.5 ml) and trifluoromethansulphonic anhydride (0.5 ml). After stirring for 1 hour, the reaction mixture was worked-up (ether) to give the title compound as an oil.
Sources & evidence
- ORD record
- ord-4ebea050bc264d27807802b2cc8fd8bb
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05401732
Reaction notes
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