Sodium borohydride → HCID 12875271, compound

HRID 1764585Notes

Reaction equation

HRID 1764585 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

HCID 4311764Sodium borohydrideHCID 1287526963826-91-5

Product 1

HCID 12875271HCID 12875271, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. extractionextracted with ethyl ether
  2. washThe combined ether extracts were washed with a solution of 5% sodium carbonate
  3. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customCrystallization from cold hexane

Sources & evidence

ORD record
ord-e746f5ea0df94f59a639aab0f59c7f67
Source dataset
uspto-grants-1978_09
Patent number
US04116975

Reaction notes

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