Sodium borohydride → (5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methanol
Reaction equation
[BH4-].[Na+].[Si:3]([O:10][CH2:11][CH2:12][C:13]1[S:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>C(O)C>[Si:3]([O:10][CH2:11][CH2:12][C:13]1[S:17][C:16]([CH2:18][OH:19])=[CH:15][CH:14]=1)([C:6]([CH3:8])([CH3:9])[CH3:7])([CH3:5])[CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Sodium borohydride (1.74 g) was added to a solution of 5-(2-(tert-butyldimethylsilyloxy)ethyl)thiophene-2-carbaldehyde (12.4 g) (example 4, step b) in ethanol (120 mL) at 0° C. The resulting solution was stirred at 0° C. for 1 h. The reaction mixture was partitioned between brine and ethyl acetate. The organic layer was separated, dried over sodium sulphate, filtered and the solvent evaporated in vacuo to give the subtitled compound. Yield 12.1 g.
Workup
- customThe reaction mixture was partitioned between brine and ethyl acetate
- customThe organic layer was separated
- dry with materialdried over sodium sulphate
- filtrationfiltered
- customthe solvent evaporated in vacuo
Sources & evidence
- ORD record
- ord-4636ec5a837b4c9789240dc07af8e414
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08629271B2
Reaction notes
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