Diazomethane → Methyl 3-methoxy-1-benzothiophene-2-carboxylate

HRID 978090Notes

Reaction equation

HRID 978090 reaction equation
[OH:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[N+](=[CH2:17])=[N-]>C(Cl)Cl>[CH3:17][O:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 9550Diazomethane2×HCID 83165Methyl 3-hydroxybenzo(b)thiophene-3-carboxylate

Product 1

HCID 88021Methyl 3-methoxy-1-benzothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred, ice-bath cooled mixture of methyl 3-hydroxybenzo[b]thiophene-2-carboxylate (J. Org. Chem. 32, 2678 (1967) (2.1 g, 0.01 m) and dry methylene chloride (25 ml) was treated with ethereal diazomethane in portions until the yellow color of the diazomethane persists, and nitrogen was no longer evolved. Concentration in vacuo yielded methyl 3-methoxybenzo[b]-thiophene-2-carboxylate as a pale tan solid; m/z 324 (M+.). The material was used without further purification in the next step.

Workup

  1. temperatureA stirred, ice-bath cooled
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-944b2aedf42a417992288918ecffac7c
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Reaction notes

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