Methanol → HCID 13787399, compound

HRID 1905958Notes

Reaction equation

HRID 1905958 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]([C:10]([OH:12])=[O:11])[CH2:8][CH2:9][C:4]=2[CH:3]=1.[CH3:13]O>>[CH3:1][C:2]1[S:6][C:5]2[CH:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:8][CH2:9][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 13588807HCID 13588807, compound

Product 1

HCID 13787399HCID 13787399, compoundYield 74%

Procedure

A solution of 9.4 g (0.051 mole) of 2-methyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acid and 0.4 g of paratoluenesulfonic acid monohydrate in 400 cc of methanol was stirred at ambient temperature for 20 hours then concentrated dry under reduced pressure. The residue was picked up with ethyl acetate. The resulting solution was washed with an aqueous solution of sodium bicarbonate then water. It was dried on sodium sulfate. After evaporation of the solvent under reduced pressure, the residue was distilled. 7.5 g (yield=74%) of methyl 2-methyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylate was obtained. Bp0.6=107° C.

Workup

  1. concentrationthen concentrated
  2. customdry under reduced pressure
  3. washThe resulting solution was washed with an aqueous solution of sodium bicarbonate
  4. customIt was dried on sodium sulfate
  5. customAfter evaporation of the solvent under reduced pressure
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-23048d5310944a88b9ff4cad4b9ab53c
Source dataset
uspto-grants-1987_03
Patent number
US04649153

Reaction notes

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