Hydrochloric Acid → HCID 20391998, compound

HRID 1863522Notes

Reaction equation

HRID 1863522 reaction equation
[CH3:1][O:2][C:3]([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:4].CC(C)([O-])C.[K+].I[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40].Cl>CS(C)=O>[CH3:1][O:2][C:3]([C:5]1([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])[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:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10858538HCID 10858538, compoundHCID 20392009HCID 20392009, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20391998HCID 20391998, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

2.88 g (7.94 mmols) of 3-methoxycarbonyl-4-(1-phenylthiotrans-2-octenyl)-oxolane-2-one and 0.98 g (8.73 mmols) of potassium t-butoxide were dissolved in 47 ml of dimethyl sulfoxide in an argon atmosphere and the mixture was stirred for 10 minutes at room temperature. A solution of 2.36 g (8.73 mmols) of methyl 7-iodoheptanoate in 3 ml of dimethyl sulfoxide was added to the above reaction mixture followed by stirring for 19 hours at room temperature. The reaction mixture was then rendered neutral with diluted hydrochloric acid while cooling with ice-water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The extract was filtered and the solvent was removed from the filtrate under reduced pressure. The residue thus obtained was purified by silica gel column chromatography using a mixture of ethyl acetate and n-hexane as an eluent to obtain 3.93 g (98% yield) of 3-methoxycarbonyl-3-(6-methoxycarbonylhexyl)-4-(1-phenylthio-trans- 2-octenyl)-oxolane-2-one as an oily substance.

Workup

  1. stirringby stirring for 19 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe extract was filtered
  6. customthe solvent was removed from the filtrate under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography
  9. additiona mixture of ethyl acetate and n-hexane as an eluent

Sources & evidence

ORD record
ord-aa4b0b21094c4300b70a17399a1c2f55
Source dataset
uspto-grants-1979_09
Patent number
US04169199

Reaction notes

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