Acetic Acid → (+/-)-(5Z)-7-{(1R,2R,3R,5R)-5-chloro-2-[(E)-4,4-dimethyl-3-oxo-1-octenyl]-3-(tetrahydropyran-2-yloxy)-cyclopentyl}-5-heptenic acid methyl ester

HRID 1382531

Reaktionsgleichung

Reaktionsgleichung von HRID 1382531
[H-].[Na+].COP([CH2:9][C:10](=[O:18])[C:11]([CH3:17])([CH3:16])[CH2:12][CH2:13][CH2:14][CH3:15])(=O)OC.[CH3:19][O:20][C:21](=[O:43])[CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][C@H:28]1[C@H:32]([Cl:33])[CH2:31][C@@H:30]([O:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[C@@H:29]1[CH:41]=O.C(O)(=O)C>C(COC)OC.O1CCCC1.C(OCC)C.O>[CH3:19][O:20][C:21](=[O:43])[CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][C@H:28]1[C@H:32]([Cl:33])[CH2:31][C@@H:30]([O:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[C@@H:29]1/[CH:41]=[CH:9]/[C:10](=[O:18])[C:11]([CH3:16])([CH3:17])[CH2:12][CH2:13][CH2:14][CH3:15]

Komponenten

9

Edukt 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 11234130methyl (5Z)-7-[(1R,2R,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]-5-heptenoateHCID 13018035Dimethyl (3,3-dimethyl-2-oxoheptyl)phosphonate

Produkt 1

HCID 13853246(+/-)-(5Z)-7-{(1R,2R,3R,5R)-5-chloro-2-[(E)-4,4-dimethyl-3-oxo-1-octenyl]-3-(tetrahydropyran-2-yloxy)-cyclopentyl}-5-heptenic acid methyl esterAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

294 mg of 55% sodium hydride is suspended in 25 ml of dimethoxyethane, and 1.53 g of 3,3-dimethyl-2-oxoheptanephosphonic acid dimethyl ester is instilled. It is stirred for another 30 minutes, cooled to -20° C., and a solution of 1.98 g of VII in instilled in 10 ml of dimethoxyethane and 10 ml of tetrahydrofuran. After 1 hour it is allowed to warm to room temperature, mixed with 0.5 ml of glacial acetic acid, diluted with 200 ml of diethyl ether, shaken three times with 20 ml of salt water each, dried over magnesium sulfate and evaporated in a vacuum to dryness. The residue is chromatographed on silica gel with hexane/5-25% diethyl ether. 1.62 g of VIII is obtained as colorless oil. IR: 2998, 2955, 2863, 1730, 1684, 1621, 1437, 1060, 978/cm.

Aufarbeitung

  1. waitAfter 1 hour it is allowed
  2. temperatureto warm to room temperature
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in a vacuum to dryness
  5. customThe residue is chromatographed on silica gel with hexane/5-25% diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-48d6969b3e31458bb371923dbbf040b3
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04806668

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