Water → 4-(Dimethylaminomethyl)-2-thiophenemethanol

HRID 851104Notes

Reaction equation

HRID 851104 reaction equation
[OH:1][CH2:2][C:3]1[S:7][CH:6]=[C:5]([C:8]([N:10]([CH3:12])[CH3:11])=O)[CH:4]=1.[H-].[Al+3].[H-].[H-].O>O1CCCC1.Cl>[CH3:12][N:10]([CH2:8][C:5]1[CH:4]=[C:3]([CH2:2][OH:1])[S:7][CH:6]=1)[CH3:11]

Participants

6

Reactant 3

HCID 962WaterHCID 212890685-(Hydroxymethyl)-N,N-dimethyl-3-thiophenecarboxamideHCID 21584524Aluminiumhydride

Product 1

HCID 129265384-(Dimethylaminomethyl)-2-thiophenemethanol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-(hydroxymethyl)-N,N-dimethyl-3-thiophenecarboxamide (1.7 g) in dry tetrahydrofuran (150 ml) was treated with a 0.5 M solution of aluminium hydride in tetrahydrofuran (26 ml). After 2 h at room temperature, water (5 ml) was cautiously added and the mixture was filtered through diatomaceous earth. The filtrate was evaporated to leave an oily residue, which was dissolved in 2 M hydrochloric acid (20 ml). The aqueous solution was washed with diethyl ether, basified with 5 M sodium hydroxide and extracted with ethyl acetate.

Workup

  1. filtrationthe mixture was filtered through diatomaceous earth
  2. customThe filtrate was evaporated
  3. customto leave an oily residue, which
  4. washThe aqueous solution was washed with diethyl ether
  5. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-0d89dcde9c6e498190a3e7dd5a2c5d76
Source dataset
uspto-grants-1983_05
Patent number
US04382929

Reaction notes

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