Potassium bisulfate → Ethyl 2-(mercaptomethyl)-1,4-dithiaspiro[4.4]nonane-7-acetate

HRID 1608271Notes

Reaction equation

HRID 1608271 reaction equation
C([S:4][CH2:5][CH:6]1[CH2:10][S:9][C:8]2([CH2:14][CH2:13][CH:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11]2)[S:7]1)(=O)C.[O-]CC.[Na+].OS([O-])(=O)=O.[K+]>C(O)C>[SH:4][CH2:5][CH:6]1[CH2:10][S:9][C:8]2([CH2:14][CH2:13][CH:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11]2)[S:7]1

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 2723922Sodium ethoxideHCID 19849041Ethyl 2-[(acetylthio)methyl]-1,4-dithiaspiro[4.4]nonane-7-acetate

Product 1

HCID 19849025Ethyl 2-(mercaptomethyl)-1,4-dithiaspiro[4.4]nonane-7-acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Example F and sodium ethoxide (prepared from 350 mg of sodium metal) in absolute ethanol (40 ml) was stirred for 1 hr under nitrogen. The reaction mixture was poured into 200 ml of 0.5N KHSO4 and extracted with ethyl acetate. After drying the organic phase over sodium sulfate, the solvent was removed on the rotary evaporator and the residue was chromatographed on silica gel using 5% ethyl acetate/hexane to give 2.1 g of the titled compound.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialAfter drying the organic phase over sodium sulfate
  3. customthe solvent was removed on the rotary evaporator
  4. customthe residue was chromatographed on silica gel using 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-fb6a974e800d4575a8cbbc0854a4e0e6
Source dataset
uspto-grants-1989_09
Patent number
US04870098

Reaction notes

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