Reaction #1692

Reaction equation

2-cyano-5-formyl-thiophene

sodium borohydride

→

2-cyano-5-(hydroxymethyl)thiophene

Yield 88.0%

Solvents

EtOH

Conditions

Workup

1. 1
   Otherthe solvent was removed in vacuo
2. 2
   Otherthe residue was partitioned between ethyl acetate and brine
3. 3
   OtherThe layers were separated
4. 4
   Washthe organic phase was washed once with 1M citric acid and once with brine
5. 5
   Dryingdried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo

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.

Source