Thiophenol → HCID 70629228, compound

HRID 839273Notes

Reaction equation

HRID 839273 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[CH3:14][O:15][C:16]([C:18]12[CH2:23][CH:22]1[CH2:21][CH2:20][C:19]2=[O:24])=[O:17]>C(O)(C)(C)C>[CH3:14][O:15][C:16]([C:18]1[C:19](=[O:24])[CH2:20][CH2:21][C:22]=1[CH2:23][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:17]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 12881134Methyl 2-oxobicyclo[3.1.0]hexane-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 70629228HCID 70629228, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

Thiophenol (660 mg: 6 mmol) was added to a solution of potassium t-butoxide (650 mg: 6 mmol) in 5 ml of t-butyl alcohol. The mixture was stirred for 10 minutes. A solution of 2-oxo-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester of Preparation 2(924 mg, 6 mmol) in 2 ml of t-butyl alcohol was added to the mixture. After stirring the mixture at room temperature for about 30 minutes, most of the solvent was distilled off under reduced pressure. Ether was added to the residue and dilute hydrochloric acid was added to acidify the solution, and the ethereal solution was washed with a saturated aqueous solution of sodium chloride and was dried over anhydrous magnesium sulfate and was filtered. The solvent was distilled off under reduced pressure. The remaining crystals were recrystallized from ether and n-hexane to obtain 2-oxo-5-phenylthiomethyl-cyclopentenecarboxylic acid methyl ester as white crystals.

Workup

  1. additionwas added to the mixture
  2. stirringAfter stirring the mixture at room temperature for about 30 minutes
  3. distillationmost of the solvent was distilled off under reduced pressure
  4. additionEther was added to the residue and dilute hydrochloric acid
  5. additionwas added
  6. washthe ethereal solution was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationwas filtered
  9. distillationThe solvent was distilled off under reduced pressure
  10. customThe remaining crystals were recrystallized from ether and n-hexane

Sources & evidence

ORD record
ord-544096aa2ce3426196793bdb8d938baf
Source dataset
uspto-grants-1978_06
Patent number
US04094886

Reaction notes

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