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Tetrahydrofuran → (1S,5R,6R)-6-[(E)-3-Oxo-4-phenoxy-1-butenyl]-2-oxabicyclo[3,3,0]octan-3-one

HRID 1701175
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1701175
C([C@H]1CC[C@H]2[C@@H]1CC(=O)O2)=O.O1CCCC1.[Li].[O:18]=[C:19]([CH2:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)/[CH:20]=[CH:21]/[C@H:22]1[C@H:29](OC(=O)C2C=CC=CC=2)[CH2:28][C@H:27]2[C@@H:23]1[CH2:24][C:25](=[O:39])[O:26]2>C(O)(=O)C>[O:18]=[C:19]([CH2:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)/[CH:20]=[CH:21]/[C@H:22]1[CH2:29][CH2:28][C@H:27]2[C@@H:23]1[CH2:24][C:25](=[O:39])[O:26]2
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Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 3028194LithiumHCID 12767308(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoateHCID 12884327(1S,5R,6S)-6-formyl-2-oxabicyclo[3,3,0]octan-3-one

Produkt 1

HCID 22810300(1S,5R,6R)-6-[(E)-3-Oxo-4-phenoxy-1-butenyl]-2-oxabicyclo[3,3,0]octan-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 7.06 g. of (1S,5R,6S)-6-formyl-2-oxabicyclo[3,3,0]octan-3-one [E.J. Corey et al., J. Org. Chem. 39: 256 (1974)] in 450 ml. of absolute tetrahydrofuran is combined with 13.3 g. of the lithium salt of dimethyl-2-oxo-3-phenoxypropyl phosphonate (preparation: see Example 1). The mixture is stirred at room temperature under argon for 2 hours, then neutralized with glacial acetic acid, concentrated under vacuum, combined with 300 ml. of methylene chloride, and the mixture is extracted with 30 ml. of 5% sodium bicarbonate solution and then twice with respectively 30 ml. of water, dried with magnesium sulfate, and evaporated under vacuum. Recrystallization of the residue from isopropanol yields 11.0 g. (84.5% of theory) of the title compound in the form of colorless crystals.

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. extractionof methylene chloride, and the mixture is extracted with 30 ml
  3. dry with materialof water, dried with magnesium sulfate
  4. customevaporated under vacuum
  5. customRecrystallization of the residue from isopropanol
  6. customyields 11.0 g

Quellen und Nachweise

ORD-Eintrag
ord-f735cb29878546d99a5c72a4896f6852
Quelldatensatz
uspto-grants-1980_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04191823

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