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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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Reaktionsgleichung

Reaktionsgleichung von HRID 1701174
[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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Komponenten

5

Edukt 3

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

Produkt 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 benzoateAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e6a862b9576d40ce8d3e535f127f120c
Quelldatensatz
uspto-grants-1980_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04191823

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