5-Nitrothiophene-2-carboxaldehyde → (5-Nitrothiophen-2-yl)methanol
Reaction equation
[BH4-].[Na+].[OH:3][CH2:4][C:5]1[S:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1.[N+](C1SC(C=O)=CC=1)([O-])=O>O1CCCC1>[OH:3][CH2:4][C:5]1[S:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Preparation of 2-hydroxymethyl-5-nitro-thiophene Sodium borohydride (5.50 g, 145.4 mmol;) was added to a stirred, cooled solution of 5-nitro-2-thiophenecarboxaldehyde (22.0 g, 140.0 mmol) in tetrahydrofuran (500 ml). The resulting mixture was quenched with saturated aqueous ammonium chloride and warmed to room temperature. Tetrahydrofuran was removed at reduced pressure and the remaining aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulphate. The solvent was removed at reduced pressure to give 2-hydroxymethyl-5-nitro-thiophene (18.8 g, 84%) as a brown oil which was used without further purification.