Sodium borohydride → HCID 21866516, compound

HRID 1582918Notes

Reaction equation

HRID 1582918 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[S:9][C:8]([C:10]#[N:11])=[C:7]([CH3:12])[CH:6]=1)=[O:4]>C(O)C>[OH:4][CH2:3][C:5]1[S:9][C:8]([C:10]#[N:11])=[C:7]([CH3:12])[CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21866473HCID 21866473, compound

Product 1

HCID 21866516HCID 21866516, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.75 g (152 mmol) of sodium borohydride were added portionwise at room temperature to a solution of 23 g (152 mmol) of 5-formyl-3-methylthiophene-2-carbonitrile in 300 ml of absolute ethanol. The reaction mixture was stirred for 5 minutes, concentrated under a water pump vacuum, taken up in ethyl acetate and extracted with 5% strength citric acid solution and with saturated sodium chloride solution, the organic phase was dried over magnesium sulfate, the desiccant was filtered off, and the solvent was distilled off at room temperature and under a water pump vacuum. This gave 24 g of the title compound as a dark red oil which still contained solvent and which was employed in the following reactions without further purification. 1H NMR (270 MHz, DMSO-d6): δ=2.4 (s, 3H), 4.7 (m, 2H), 5.9 (m, 1H), 7.0 (s, 1H).

Workup

  1. concentrationconcentrated under a water pump vacuum
  2. extractionextracted with 5% strength citric acid solution and with saturated sodium chloride solution
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. filtrationthe desiccant was filtered off
  5. distillationthe solvent was distilled off at room temperature and under a water pump vacuum
  6. customThis gave 24 g of the title compound as a dark red oil which still contained solvent and which was employed in the following reactions without further purification

Sources & evidence

ORD record
ord-96cc55ae18324d6eb01cb52d6261274c
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

Loading…