Sodium borohydride → 5-(Hydroxymethyl)thiophene-2-carbonitrile
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
Product 1
Reagents, catalysts & solvents 1
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
- customthe solvent was removed in vacuo
- customthe residue was partitioned between ethyl acetate and brine
- customThe layers were separated
- washthe organic phase was washed once with 1M citric acid and once with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b39e2726de21401db17e5cadc1bb0672
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05707966
Reaction notes
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