Thiophene-3-carboxylic acid → Methyl 3-thiophenecarboxylate

HRID 2286510Notes

Reaction equation

HRID 2286510 reaction equation
[CH:1]1[S:5][CH:4]=[CH:3][C:2]=1[C:6]([OH:8])=[O:7].[N+](=[CH2:11])=[N-]>CCOCC>[CH3:11][O:7][C:6](=[O:8])[C:2]1[CH:3]=[CH:4][S:5][CH:1]=1

Participants

4

Reactant 2

HCID 6918Thiophene-3-carboxylic acidHCID 9550Diazomethane

Product 1

HCID 574151Methyl 3-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 3-thenoic acid (prepared as described by S. Gronowitz in Arkiv. Kemi., 7, 361-369, 1954) (4.7 g, 0.037 mole) in anhydrous ether was treated with an ethereal solution of diazomethane (from 7-8 g N-nitroso-methylurea and 40% aqueous potassium hydroxide (30 ml) and ether (100 ml)). Evaporation in vacuo gave methyl-3-thenoate (4.9 g). Lithium aluminium hydride (1.3 g) reduction in ether gave 3-hydroxymethylthiophene (3.4 g, 93%) as a colourless oil.

Workup

  1. customEvaporation in vacuo

Sources & evidence

ORD record
ord-3cf64598d61a4c33aac270963a052743
Source dataset
uspto-grants-1981_05
Patent number
US04267175

Reaction notes

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