Methanol → Methyl 5-ethoxy-6-hydroxybenzo[b]thiophene-2-carboxylate

HRID 1583578Notes

Reaction equation

HRID 1583578 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([OH:16])=[CH:6][C:7]2[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][C:8]=2[CH:15]=1)[CH3:2].[CH3:17]O.S(=O)(=O)(O)O>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[C:5]([OH:16])=[CH:6][C:7]2[S:11][C:10]([C:12]([O:14][CH3:17])=[O:13])=[CH:9][C:8]=2[CH:15]=1)[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 20259233HCID 20259233, compound

Product 1

HCID 20259234Methyl 5-ethoxy-6-hydroxybenzo[b]thiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.71 g. of 5 -ethoxy-6-hydroxybenzothiophene-2-carboxylic acid, 0.29 g. of methanol, and a catalytic amount of sulfuric acid in methylene chloride was heated to reflux for 48 hours. The solution was diluted with ethyl acetate and was washed first with a 10% aqueous sodium bicarbonate solution and then with water. The organic solution was dried over sodium sulfate and evaporated to dryness providing the desired ester intermediate which was used without further purification.

Workup

  1. temperatureto reflux for 48 hours
  2. washwas washed first with a 10% aqueous sodium bicarbonate solution
  3. dry with materialThe organic solution was dried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-418b46f9bcd943b7a73b4bda3a33152e
Source dataset
uspto-grants-1985_11
Patent number
US04552891

Reaction notes

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