Sodium hydride → HCID 22097916, Verbindung

HRID 1383192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383192
C(OP([CH:9]([F:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[CH3:16][C:17]1([CH3:32])[CH:19](/[CH:20]=C(\Br)/C(OCCC)=O)[CH:18]1[C:29]([OH:31])=[O:30].[H-].[Na+].P(O)(O)([O-])=O.[Na+]>COCCOC>[CH3:16][C:17]1([CH3:32])[CH:19](/[CH:20]=[C:9](/[F:15])\[C:10](=[O:11])[O:12][CH2:13][CH3:14])[CH:18]1[C:29]([OH:31])=[O:30]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 23672064Monosodium phosphateHCID 867427802,2-dimethyl-3(Z)-[2-bromo-2-propoxycarbonyl-ethenyl]-cyclopropane-1-carboxylic acid

Produkt 1

HCID 22097916HCID 22097916, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A solution of 7.7 g of ethyl diethyl-phosphono-fluoroacetate (prepared by process of Ann. Chem., 1964, p. 6741), 60 ml of 1,2-dimethoxyethane and 4 g of (1R, trans) 2,2-dimethyl-3-formyl-cyclopropane-carboxylic acid was added over 30 minutes at 2° to 10° C. to a suspension of 2.6 g of a 60% sodium hydride in oil suspension and 60 ml of 1,2-dimethoxyethane and the mixture was stirred at 5° C. for 15 minutes, and then at room temperature for 3 hours. The resulting solution was poured into aqueous monosodium phosphate solution at 5° C. and the mixture was stirred for 10 minutes. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to dryness at 40° C. under reduced pressure to obtain 6.5 g of an oil residue. The latter was chromatographed over silica gel and was eluted with a 70-30-1 hexane-ethyl acetate-acetic acid mixture to obtain 4 g of (1R,trans) 2,2-dimethyl-3(E)-[2-fluoro-3-oxo-3-ethoxypropenyl]-cyclopropane-1-carboxylic acid

Aufarbeitung

  1. waitat room temperature for 3 hours
  2. stirringthe mixture was stirred for 10 minutes
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with water
  5. customdried
  6. customevaporated to dryness at 40° C. under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2b2e8cdea1794c64ba0aa8beb516aa55
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04808749

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