Hydrochloric Acid → HCID 20391996, compound

HRID 1863523Notes

Reaction equation

HRID 1863523 reaction equation
COC([C:5]1([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:9]([CH:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:8][O:7][C:6]1=[O:25])=O.[C-]#N.[Na+].Cl>CN(C)P(=O)(N(C)C)N(C)C>[CH3:35][O:34][C:32]([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:5]1[CH:9]([CH:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:8][O:7][C:6]1=[O:25])=[O:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 20391998HCID 20391998, compound

Product 1

HCID 20391996HCID 20391996, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

1.00 g (1.98 mmol) of 3-methoxycarbonyl-3-(6-methoxycarbonylhexyl)-4-(1-phenylthio-trans-2-octenyl)-oxolane-2-one was dissolved in 23 ml of hexamethylphosphoric triamide followed by stirring. 194 mg (3.96 mmols) of sodium cyanide was then added to the solution and the mixture was heated at 75° to 80° C. for 15 hours while heating. The mixture was allowed to cool to room temperature and rendered neutral with diluted hydrochloric acid. The mixture was extracted with ethyl acetate and the extract was washed three times with water and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation and the resulting residue was purified by silica gel column chromatography using ethyl acetate and n-hexane (1:9 by volume) as an eluent to obtain 730 mg (83% yield) of 3-(6-methoxycarbonylhexyl)-4-(1-phenylthio-trans-2-octenyl)-oxolane-2-one an an oily substance.

Workup

  1. temperaturethe mixture was heated at 75° to 80° C. for 15 hours
  2. temperaturewhile heating
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed three times with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then removed by distillation
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fc3509da4a024e10bf4343a62b76c22e
Source dataset
uspto-grants-1979_09
Patent number
US04169199

Reaction notes

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