Ethanol → HCID 13588808, compound

HRID 1905957Notes

Reaction equation

HRID 1905957 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.S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[CH2:18]([O:11][C:10]([CH:7]1[C:5]2[S:6][C:2]([CH3:1])=[CH:3][C:4]=2[CH2:9][CH2:8]1)=[O:12])[CH3:19]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 13588807HCID 13588807, compound

Product 1

HCID 13588808HCID 13588808, compoundYield 81%

Procedure

A solution of 19.3 g of 2-methyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acid and 10 cc of sulfuric acid in 500 cc of ethanol was refluxed for 8 hours then concentrated under reduced pressure to a volume of 100 cc. The residue was diluted with ethyl acetate and stirred with an aqueous solution of sodium bicarbonate. The organic phase was separated, washed with water and dried over sodium sulfate. After evaporation of the solvent under reduced pressure the residue was distilled. 18.2 g (yield=81%) of ethyl-2-methyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylate was obtained. Bp0.7=90° C.

Workup

  1. concentrationthen concentrated under reduced pressure to a volume of 100 cc
  2. additionThe residue was diluted with ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customAfter evaporation of the solvent under reduced pressure the residue
  7. distillationwas distilled

Sources & evidence

ORD record
ord-5f306c0e298f4d7abddccfde8fbf53e0
Source dataset
uspto-grants-1987_03
Patent number
US04649153

Reaction notes

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