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Diethyl Ether → 2-Methyl-3-phenylbenzyl 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylate

HRID 1607366
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1607366
[CH3:1][C:2]1([CH3:34])[CH:4]([CH:5](OC(=O)C)[C:6](Cl)([Cl:11])[C:7]([F:10])([F:9])[F:8])[CH:3]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:22]=1[CH3:33])=[O:18].C(OCC)C.CCCCC>CN(C=O)C.[Zn]>[CH3:1][C:2]1([CH3:34])[CH:4]([CH:5]=[C:6]([Cl:11])[C:7]([F:8])([F:9])[F:10])[CH:3]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:22]=1[CH3:33])=[O:18]
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Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 8003PentaneHCID 13933704(2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-acetoxy-2,2-dichloro-3,3,3-trifluoro-propyl)cyclopropanecarboxylate

Produkt 1

HCID 549012-Methyl-3-phenylbenzyl 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994
Zinc
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 38.4 mg (0.074 mmol) of the stereoisomer [RF 0.39 (CH2Cl2 /hexane=1/1)] of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-acetoxy-2,2-dichloro-3,3,3-trifluoro-propyl)cyclopropanecarboxylate obtained in Example 11 and dissolved in 0.3 ml of DMF, 6 mg of zinc powder was added, and the mixture was stirred at 60° C. for 2.5 hours. After an addition of 2 ml of diethyl ether and 2 ml of pentane to the mixture, the inorganic salt was filtered off through a silica gel short column. The silica gel was washed with diethyl ether, and the organic layers were combined and concentrated under reduced pressure. The product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/2) to obtain 29.8 mg of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)cyclopropanecarboxylate as a colorless oily substance.

Aufarbeitung

  1. filtrationthe inorganic salt was filtered off through a silica gel short column
  2. washThe silica gel was washed with diethyl ether
  3. concentrationconcentrated under reduced pressure
  4. customThe product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-1d450ce8d5fd45079b87b63cb33d67fd
Quelldatensatz
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04864052

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