Sodium borohydride → HCID 12875271, compound
Reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:8]=[O:9])[S:5][C:6]=1[CH3:7].[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH2:8][OH:9])[S:5][C:6]=1[CH3:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
11.8 G. of 4-bromo-3,5-dimethylthiophene-2-carboxaldehyde was dissolved in 250 ml. of dry ethanol and stirred at 20° C. 0.52 G. of sodium borohydride was added and the resulting solution was stirred for 30 minutes, then poured into ice water and extracted with ethyl ether. The combined ether extracts were washed with a solution of 5% sodium carbonate and a saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. Crystallization from cold hexane yielded 4-bromo-3,5-dimethyl-2-hydroxymethylthiophene, m.p. 85°-90° C.
Workup
- extractionextracted with ethyl ether
- washThe combined ether extracts were washed with a solution of 5% sodium carbonate
- dry with materiala saturated sodium chloride solution, dried over sodium sulfate
- filtrationfiltered
- customevaporated
- customCrystallization from cold hexane
Sources & evidence
- ORD record
- ord-1f71358accda41d9ba5dd9c88d15a993
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04256878
Reaction notes
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