Ethanol → (5-nitrothiophen-2-yl)methanol

HRID 861880Notes

Reaction equation

HRID 861880 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[S:10][C:9]([CH:11]=[O:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].C(O)C>O>[OH:12][CH2:11][C:9]1[S:10][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 782815-Nitrothiophene-2-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 332588(5-nitrothiophen-2-yl)methanolYield 49.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium borohydride (0.24 g) was added to a mixture of 5-nitro-2-thiophenecarboxaldehyde (1.0 g) and ethanol (30 ml) at 0° C. and then this mixture was stirred at the same temperature for 40 minutes. The reaction mixture was poured into water and extracted with dichloromethane. The dichloromethane layer was washed with water and dried (MgSO4), after which the solvent was evaporated off, to yield 2-hydroxymethyl-5-nitrothiophene (0.5 g, 49%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe dichloromethane layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customafter which the solvent was evaporated off

Sources & evidence

ORD record
ord-fef0c22ab45f4222947122e29012b79a
Source dataset
uspto-grants-1998_02
Patent number
US05716944

Reaction notes

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