Water → 5-(Dimethylaminomethyl)-3-thiophenemethanol

HRID 867923Notes

Reaction equation

HRID 867923 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]([C:5]1[S:9][CH:8]=[C:7]([C:10](OC)=[O:11])[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[CH3:14][N:2]([CH2:3][C:5]1[S:9][CH:8]=[C:7]([CH2:10][OH:11])[CH:6]=1)[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 12926528Methyl 5-[(dimethylamino)carbonyl]-3-thiophenecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 129264995-(Dimethylaminomethyl)-3-thiophenemethanolYield 99.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of methyl 5-[(dimethylamino)carbonyl]-3-thiophenecarboxylate (0.5 g) in dry diethylether (50 ml) was added to a slurry of lithium aluminium hydride (0.3 g) in dry diethylether (100 ml). The mixture was stirred for 3 hours at room temperature. Water was cautiously added, the mixture was filtered and the filtrate was evaporated to give the title compound (0.4 g) as a colourless oil b.p. 120°/0.1 mm. The oxalate was formed in and recrystallised from ethanol m.p. 107°-8°.

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-cd6d9fd672854bc3803d5a3ed4c8f612
Source dataset
uspto-grants-1988_10
Patent number
US04777179

Reaction notes

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