Water → 2,2-Dimethyl-3-(2-phenyl-vinyl)-cyclopropanecarboxylic acid ethyl ester

HRID 64920

Reaktionsgleichung

Reaktionsgleichung von HRID 64920
C(OP([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)OCC)C.C([Li])CCC.[CH2:21]([O:23][C:24]([CH:26]1[CH:28]([CH:29]=O)[C:27]1([CH3:32])[CH3:31])=[O:25])[CH3:22].O>O1CCCC1.CCCCCC>[CH2:21]([O:23][C:24]([CH:26]1[CH:28]([CH:29]=[CH:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:27]1([CH3:31])[CH3:32])=[O:25])[CH3:22]

Komponenten

7

Edukt 4

HCID 962WaterHCID 14122Diethyl benzylphosphonateHCID 566079Ethyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylateHCID 178418339Butyllithium

Produkt 1

HCID 544855342,2-Dimethyl-3-(2-phenyl-vinyl)-cyclopropanecarboxylic acid ethyl esterAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

22.8 g (0.1 mol) of benzylphosphonic acid diethyl ester were dissolved in 400 ml of absolute tetrahydrofuran and the solution was cooled to -70° C. 0.11 mol of n-butyl-lithium (as a 15% strength solution in hexane) were added dropwise under a counter-current of nitrogen and while stirring well; the mixture was then stirred at -70° C. for a further 15 minutes, and thereafter 18.6 g (0.1 mol) of 2,2-dimethyl-3-formyl-cyclopropanecarboxylic acid ethyl ester were added dropwise at -65° C., again still under nitrogen. The reaction mixture was then allowed to come to room temperature and was stirred further for 3 hours at 25° C. Thereafter, the reaction batch was poured into 2 liters of water and extracted with 600 ml of ether. The ether phase was dried over sodium sulphate and the solvent was then stripped off in vacuo. The oily residue was distilled at 145°-150° C./3 mm Hg. 2,2 -Dimethyl-3-(2-phenyl-vinyl)-cyclopropanecarboxylic acid ethyl ester having a refractive index nD23 of 1.5022 was obtained in 69.6% yield.

Aufarbeitung

  1. stirringthe mixture was then stirred at -70° C. for a further 15 minutes
  2. customto come to room temperature
  3. stirringwas stirred further for 3 hours at 25° C
  4. extractionextracted with 600 ml of ether
  5. dry with materialThe ether phase was dried over sodium sulphate
  6. distillationThe oily residue was distilled at 145°-150° C./3 mm Hg

Quellen und Nachweise

ORD-Eintrag
ord-d51ec3015d224f0e8d1942f2149d546a
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04611009

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