Pyridine → 2-chloro-6-fluorobenzyl(+/-)-cis-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylate

HRID 1285388

Reaktionsgleichung

Reaktionsgleichung von HRID 1285388
Cl[C:2]([C@H:4]1[C@@H:6](/[CH:7]=[C:8](\[Cl:13])/[C:9]([F:12])([F:11])[F:10])[C:5]1([CH3:15])[CH3:14])=[O:3].[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:18]=1[CH2:19][OH:20].N1C=CC=CC=1.C1(C)C=CC=CC=1>C(OCC)C>[Cl:13]/[C:8](/[C:9]([F:12])([F:11])[F:10])=[CH:7]\[C@@H:6]1[C@H:4]([C:2]([O:20][CH2:19][C:18]2[C:21]([F:25])=[CH:22][CH:23]=[CH:24][C:17]=2[Cl:16])=[O:3])[C:5]1([CH3:15])[CH3:14]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 1140TolueneHCID 918682-Chloro-6-fluorobenzyl alcoholHCID 11334477(1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride

Produkt 1

HCID 1317145102-chloro-6-fluorobenzyl(+/-)-cis-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylateAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of (±)-cis-1-chlorocarbonyl-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane (0.82 g), 2-chloro-6-fluorobenzyl alcohol (1.0 g), pyridine (0.275 g) and dry toluene (50 ml) was stirred at the ambient temperature (ca. 25° C.) for a period of 6 hours and then kept for a further period of 72 hours without stirring. The mixture was diluted with diethyl ether (350 ml) and the resultant mixture washed with water, with dilute aqueous sodium carbonate solution, and then dried over anhydrous magnesium sulphate. The solvents were evaporated and the residual oil purified by preparative thick layer chromatography using silica gel plates and diethyl ether as eluent. The oil which was obtained was then distilled to yield 2-chloro-6-fluorobenzyl(±)-cis-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylate (0.67 g) b.p. 150°/0.05 mm Hg.

Aufarbeitung

  1. waitkept for a further period of 72 hours
  2. stirringwithout stirring
  3. washthe resultant mixture washed with water, with dilute aqueous sodium carbonate solution
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customThe solvents were evaporated
  6. customthe residual oil purified by preparative thick layer chromatography
  7. customThe oil which was obtained
  8. distillationwas then distilled

Quellen und Nachweise

ORD-Eintrag
ord-bf7e88d1d9194f63a1b95ac782fe02b5
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04567199

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