HCID 10634057, compound → Methyl 5-(2-thioethyl)thiophene-2-carboxylate

HRID 430534Notes

Reaction equation

HRID 430534 reaction equation
C([S:4][CH2:5][CH2:6][C:7]1[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=1)(=O)C>Cl.O>[CH3:15][O:14][C:12]([C:10]1[S:11][C:7]([CH2:6][CH:5]=[S:4])=[CH:8][CH:9]=1)=[O:13]

Participants

4

Reactant 1

HCID 10634057HCID 10634057, compound

Product 1

HCID 18350731Methyl 5-(2-thioethyl)thiophene-2-carboxylateYield 98.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 4.89 g (20 mmol) of 9d in 1N methanolic HCl (75 mL) was heated at reflux for 2 hours. The reaction was diluted with water (50 mL) and the methanol was removed by concentration, in vacuo. The aqueous residue was extracted with ether (2×75 mL). The combined organic extracts were dried over Na2SO4 and concentrated, in vacuo, to provide the product as a yellow oil (3.93 g, 97% yield).

Workup

  1. temperatureat reflux for 2 hours
  2. customthe methanol was removed by concentration, in vacuo
  3. extractionThe aqueous residue was extracted with ether (2×75 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated, in vacuo

Sources & evidence

ORD record
ord-352334c05a5c4e5083f176ef41dda4f5
Source dataset
uspto-grants-2001_11
Patent number
US06323210B2

Reaction notes

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