5-Dimethylthiocarbamoyloxy-benzofuran-2-carboxylic acid methyl ester → Methyl 5-hydroxybenzofuran-2-carboxylate

HRID 984107Notes

Reaction equation

HRID 984107 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14]C(=S)N(C)C)=[CH:10][C:8]=2[CH:9]=1)=[O:4]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:8]=2[CH:9]=1)=[O:4]

Participants

3

Reactant 1

HCID 207660095-Dimethylthiocarbamoyloxy-benzofuran-2-carboxylic acid methyl ester

Product 1

HCID 12208973Methyl 5-hydroxybenzofuran-2-carboxylateYield 64.2%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of 5-dimethylthiocarbamoyloxy-benzofuran-2-carboxylic acid methyl ester (1.3 g, 4.7 mmol) in 25 mL diphenyl ether was heated at reflux for 2.5 hours. The reaction mixture was then cooled and the resulting precipitate collected. Purification by flash column chromatography (gradient elution: 100% hexanes to 45% EtOAc/hexanes), gave the title compound (0.58 g, 45%) as a brown solid.

Workup

  1. temperatureat reflux for 2.5 hours
  2. temperatureThe reaction mixture was then cooled
  3. customthe resulting precipitate collected
  4. customPurification
  5. washby flash column chromatography (gradient elution: 100% hexanes to 45% EtOAc/hexanes)

Sources & evidence

ORD record
ord-066f150d61c14a148738f5535dffe990
Source dataset
uspto-grants-2005_03
Patent number
US06867224B2

Reaction notes

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