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

HRID 726664

Reaction equation

HRID 726664 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-a713b903bc31442288d3b8f3fff8e84a
Source dataset
uspto-grants-1998_01
Patent number
US05710130

Linked notes

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