Hydrochloric Acid → HCID 13946785, compound
Reaction equation
COC([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.[Cl-].[Li+].Cl>CN(C)P(=O)(N(C)C)N(C)C>[C:19]1([S:18][CH:10]([CH:9]2[CH2:8][O:7][C:6](=[O:25])[CH2:5]2)/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
60 mg (0.17 mmol) of 3-methoxycarbonyl-4-(1-phenylthio-trans-2-octenyl)-oxolane-2-one was dissolved in 2 ml of hexamethyl phosphoric triamide in an argon atmosphere, and 36 mg (0.85 mmol) of lithium chloride was added to the solution followed by heating at a temperature of 100° C. for 5 hours with stirring. The reaction mixture was then allowed to cool to room temperature and decomposed with dilute hydrochloric acid. The mixture was extracted with ethyl acetate, and the extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The mixture was filtered and the filtrated was concentrated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to obtain 4-(1-phenylthio-trans-2-octenyl)-oxolane-2-one.
Workup
- additionwas added to the solution
- temperatureto cool to room temperature
- extractionThe mixture was extracted with ethyl acetate
- washthe extract was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe mixture was filtered
- concentrationthe filtrated was concentrated under reduced pressure
- customThe resulting residue was then purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-72a5f5b514a5431ea64686ad37628917
- Source dataset
- uspto-grants-1979_09
- Patent number
- US04169199
Reaction notes
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