Réaction #1692

Équation de réaction

2-cyano-5-formyl-thiophene

sodium borohydride

→

2-cyano-5-(hydroxymethyl)thiophene

Rendement 88.0%

Solvants

EtOH

Conditions de réaction

Traitement

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

Mode opératoire

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