Water → 5-(Dimethylaminomethyl)-3-thiophenemethanol

HRID 851101Notes

Reaction equation

HRID 851101 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:9][CH:8]=[C:7]([C:10](OC)=[O:11])[CH:6]=1)[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[CH3:3][N:2]([CH2:4][C:5]1[S:9][CH:8]=[C:7]([CH2:10][OH:11])[CH:6]=1)[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 12926495Methyl 5-(dimethylaminomethyl)-3-thiophenecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 129264995-(Dimethylaminomethyl)-3-thiophenemethanolYield 93.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of methyl 5-(dimethylaminomethyl)-3-thiophenecarboxylate (1.5 g) in diethylether (50 ml) was treated with lithium aluminium hydride (0.21 g). After 1 hour water (2 ml) was added and the solution was filtered through diatomaceous earth. Evaporation of the filtrate gave an oily residue which distilled to give the title compound as an oil (1.2 g) b.p. (120°/0.1 mm).

Workup

  1. filtrationthe solution was filtered through diatomaceous earth
  2. customEvaporation of the filtrate
  3. customgave an oily residue which
  4. distillationdistilled

Sources & evidence

ORD record
ord-e5644aad502747e99e8334dc2521b994
Source dataset
uspto-grants-1983_05
Patent number
US04382929

Reaction notes

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