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Water → (3aR,4R,5R,6aS)-4-((E)-4,4-Difluoro-3-oxooct-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

HRID 1943066
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Reaktionsgleichung

Reaktionsgleichung von HRID 1943066
COP([CH2:7][C:8](=[O:16])[C:9]([F:15])([F:14])[CH2:10][CH2:11][CH2:12][CH3:13])(=O)OC.O.[OH-].[Li+].O.[O:21]=[C:22]1[O:26][C@H:25]2[CH2:27][C@@H:28]([O:32][C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:34])[C@H:29]([CH:30]=O)[C@H:24]2[CH2:23]1>COC(C)(C)C>[F:15][C:9]([F:14])([CH2:10][CH2:11][CH2:12][CH3:13])[C:8](=[O:16])/[CH:7]=[CH:30]/[C@@H:29]1[C@@H:24]2[C@@H:25]([O:26][C:22](=[O:21])[CH2:23]2)[CH2:27][C@H:28]1[O:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34]
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Komponenten

6

Edukt 4

HCID 962Water2×HCID 168937Lithium hydroxide, monohydrateHCID 11000244(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoateHCID 11118722Dimethyl (3,3-difluoro-2-oxoheptyl)phosphonate

Produkt 1

HCID 68482600(3aR,4R,5R,6aS)-4-((E)-4,4-Difluoro-3-oxooct-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate
Ausbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

To a solution of dimethyl (3,3-difluoro-2-oxoheptyl)phosphonate (1) (0.378 g, 1.50 mmol) in t-butyl methyl ether (5 ml), lithium hydroxide monohydrate (60.8 mg, 1.45 mmol) was added and the mixture was stirred for one hour at room temperature. Water (0.15 ml) and (3aR,4R,5R,6aS)-2-oxo-5-phenylcarbonyloxyhexahydro cyclopenta[b]furan-4-carbaldehyde (10) (0.274 g, 1.00 mmol) were added thereto and the mixed solution was stirred for approximately 3 hours at room temperature. The reaction mixture was added to water and extracted twice with t-butyl methyl ether. The organic layers were combined, sequentially washed with water, saturated sodium bicarbonate water and saturated aqueous sodium chloride, and then dried with anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (Fuji Silysia BW-300: 100 g; ethyl acetate:hexane=1:2), to give (3aR,4R,5R,6aS)-4-((E)-4,4-difluoro-3-oxo-1-octenyl)-2-oxo-5-phenylcarbonyloxyhexahydrocyclopenta[b]furan (11) (0.201 g; 0.495 mmol; yield: 49.5%) as a colorless oil.

Aufarbeitung

  1. stirringthe mixed solution was stirred for approximately 3 hours at room temperature
  2. extractionextracted twice with t-butyl methyl ether
  3. washsequentially washed with water, saturated sodium bicarbonate water and saturated aqueous sodium chloride
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (Fuji Silysia BW-300: 100 g; ethyl acetate:hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-747583af07184429bfaae26eebf5e368
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08389748B2

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