Ethanethiol → HCID 22118376, compound

HRID 1275467Notes

Reaction equation

HRID 1275467 reaction equation
C[O-].[Na+].[CH2:4]([SH:6])[CH3:5].[CH3:7][C:8]1([CH3:31])[CH:17](OS(C)(=O)=O)[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:24]([O:26]CC)=[O:25])[C:15]=2[CH3:23])[S:10](=[O:30])(=[O:29])[CH2:9]1>CO.C(OCC)(=O)C>[CH3:7][C:8]1([CH3:31])[CH:17]([S:6][CH2:4][CH3:5])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:24]([OH:26])=[O:25])[C:15]=2[CH3:23])[S:10](=[O:29])(=[O:30])[CH2:9]1

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 10942334Sodium MethoxideHCID 22118429HCID 22118429, compound

Product 1

HCID 22118376HCID 22118376, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A methanolic solution of 0.8 g (4 mmol, 3 eq.) containing about 28 wt % sodium methoxide was diluted with 5 ml of anhydrous methanol, and 0.5 ml (6.8 mmol, 1.5 eq.) of ethanethiol was added. The mixture was stirred at room temperature for 5 minutes, and then 0.5 g (1.3 mmol) of 3,3,5-trimethyl-4-methanesulfonyloxy-6-ethoxycarbonylthiochroman-1,1-dioxide was added. The mixture was refluxed for 8 hours, and allowed to stand at room temperature for 5 days. The reaction mixture was diluted with 100 ml of ethyl acetate and washed with 50 ml of water twice, and an aqueous layer was separated and cooled in an ice bath. The aqueous layer was acidified with 5 wt % hydrochloric acid and extracted with 100 ml of ethyl acetate, and an organic layer was dried over sodium sulfate. The solvent was distilled off, and the residue was dried under reduced pressure to give 0.32 g (yield 75%) of a yellowish solid.

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed for 8 hours
  3. waitto stand at room temperature for 5 days
  4. washwashed with 50 ml of water twice
  5. customan aqueous layer was separated
  6. temperaturecooled in an ice bath
  7. extractionextracted with 100 ml of ethyl acetate
  8. dry with materialan organic layer was dried over sodium sulfate
  9. distillationThe solvent was distilled off
  10. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-9d9ce6a30c3148918bc78a8bc8e9295b
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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