5-Nitrothiophene-2-carboxaldehyde → (5-nitrothiophen-2-yl)methanol

HRID 363509Notes

Reaction equation

HRID 363509 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]=1

Participants

4

Reactant 2

HCID 782815-Nitrothiophene-2-carboxaldehydeHCID 1317211312-hydroxymethyl-5-nitro-thiophene Sodium borohydride

Product 1

HCID 332588(5-nitrothiophen-2-yl)methanolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. additionwas added to a stirred
  2. customThe resulting mixture was quenched with saturated aqueous ammonium chloride
  3. customTetrahydrofuran was removed at reduced pressure
  4. extractionthe remaining aqueous layer was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-226a69b982da41038afc4b1abdc20d59
Source dataset
uspto-grants-1999_02
Patent number
US05874472

Reaction notes

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