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Hydrochloric Acid → HCID 20391998, 화합물

HRID 1863522
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HRID 1863522 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

HCID 20391998HCID 20391998, 화합물수율 98.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매
2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aa4b0b21094c4300b70a17399a1c2f55
출처 데이터셋
uspto-grants-1979_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04169199

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