Sodium borohydride → 5-(Hydroxymethyl)thiophene-2-carbonitrile

HRID 1416584Notes

Reaction equation

HRID 1416584 reaction equation
[C:1]([C:3]1[S:4][C:5]([CH:8]=[O:9])=[CH:6][CH:7]=1)#[N:2].[BH4-].[Na+]>CCO>[C:1]([C:3]1[S:4][C:5]([CH2:8][OH:9])=[CH:6][CH:7]=1)#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 122800045-Formylthiophene-2-Carbonitrile

Product 1

HCID 106068135-(Hydroxymethyl)thiophene-2-carbonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-cyano-5-formyl-thiophene (6.9 g, 50 mmol) in EtOH (100 mL) was added sodium borohydride (1.9 g, 50 mmol) in portions. After 5 min of stirring, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and brine. The layers were separated and the organic phase was washed once with 1M citric acid and once with brine, then dried (MgSO4), filtered and concentrated in vacuo to give 6.1 g (88%) of 2-cyano-5-(hydroxymethyl)thiophene.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and brine
  3. customThe layers were separated
  4. washthe organic phase was washed once with 1M citric acid and once with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3405a54db4254f04a559d424a0b6675b
Source dataset
uspto-grants-1999_06
Patent number
US05914319

Reaction notes

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