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Lithium → (3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

HRID 1701174
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HRID 1701174 반응식
[CH:1]([C@H:3]1[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:20])[O:7]2)=O.[Li].P(=O)([O-])O[CH2:24][C:25](=[O:36])[C:26](C)(C)[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1>[O:36]=[C:25]([CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)/[CH:24]=[CH:1]/[C@H:3]1[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:20])[O:7]2
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참가 물질

5

반응물 3

HCID 3028194LithiumHCID 11000244(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoateHCID 178458319HCID 178458319, 화합물

생성물 1

HCID 12767308(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate수율 87.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

실험 절차

A solution of 548 mg. of (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one [J. Amer. Chem. Soc. 96: 5865 (1974)] in 20 ml. of absolute tetrahydrofuran is combined with 581 mg. of the lithium salt of dimethyl-2-oxo-3-phenoxypropyl phosphonate, and the mixture is agitated for 1.5 hours at room temperature under argon. The mixture is then combined with 0.3 ml. of glacial acetic acid, concentrated under vacuum, mixed with 100 ml. of methylene chloride, and extracted with 10 ml. of 5% sodium bicarbonate solution and twice with respectively 10 ml. of water. The product is dried with magnesium sulfate, evaporated under vacuum, and the residue of the evaporation is recrystallized from methylene chloride-isopropyl ether, thus obtaining 710 mg. of the title compound as colorless crystals (yield: 87.5% of theory).

후처리

  1. concentrationof glacial acetic acid, concentrated under vacuum
  2. additionmixed with 100 ml
  3. extractionof methylene chloride, and extracted with 10 ml
  4. dry with materialThe product is dried with magnesium sulfate
  5. customevaporated under vacuum
  6. customthe residue of the evaporation
  7. customis recrystallized from methylene chloride-isopropyl ether
  8. customthus obtaining 710 mg

출처 및 근거

ORD 기록
ord-e6a862b9576d40ce8d3e535f127f120c
출처 데이터셋
uspto-grants-1980_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04191823

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