Sodium borohydride → 4-(Hydroxymethyl)thiophene-2-carbonitrile

HRID 1582897Notes

Reaction equation

HRID 1582897 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[S:6][CH:7]=[C:8]([CH:10]=[O:11])[CH:9]=1)#[N:4]>C(O)C>[C:3]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][OH:11])[CH:9]=1)#[N:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 122800084-Formylthiophene-2-carbonitrile

Product 1

HCID 106542884-(Hydroxymethyl)thiophene-2-carbonitrileYield 91.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.47 g (91.8 mmol) of sodium borohydride were added, a little at a time, to a suspension of 12.6 g (91.8 mmol) of 2-cyano-4-formylthiophene in 200 ml of ethanol and stirred at room temperature for 2 hours, during which process the reaction mixture slowly formed a clear solution. After concentration in vacuo, the residue was taken up in ethyl acetate, washed in succession with saturated sodium chloride solution, 5% strength citric acid and saturated sodium chloride solution, and the organic phase was dried using sodium sulfate and concentrated in vacuo. 11.7 g of almost pure product resulted (yield 91.5%).

Workup

  1. customslowly formed a clear solution
  2. concentrationAfter concentration in vacuo
  3. washwashed in succession with saturated sodium chloride solution, 5% strength citric acid and saturated sodium chloride solution
  4. customthe organic phase was dried
  5. concentrationconcentrated in vacuo
  6. custom11.7 g of almost pure product resulted (yield 91.5%)

Sources & evidence

ORD record
ord-f48aa4a236734285aa6d16481c541669
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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