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Citric Acid → (RS)-2-methyl-4-methylidene-3-ethyl-2-cyclopenten-1-yl (1R)-trans-3-(2,2-dichloro-vinyl)-2,2-dimethylcyclopropanecarboxylate

HRID 1079008
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1079008
[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C@@H:6]([C:7](Cl)=[O:8])[C:5]1([CH3:11])[CH3:10].[CH3:13][C:14]1[CH:15]([OH:22])[CH2:16][C:17](=[CH2:21])[C:18]=1[CH2:19][CH3:20].N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C@@H:6]([C:7]([O:22][CH:15]2[CH2:16][C:17](=[CH2:21])[C:18]([CH2:19][CH3:20])=[C:14]2[CH3:13])=[O:8])[C:5]1([CH3:11])[CH3:10]
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Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 1049PyridineHCID 6454308(1R,3S)-3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chlorideHCID 15389976(RS)-2-methyl-4-methylidene-3-ethylcyclopent-2-en-1-ol

Produkt 1

HCID 15389982(RS)-2-methyl-4-methylidene-3-ethyl-2-cyclopenten-1-yl (1R)-trans-3-(2,2-dichloro-vinyl)-2,2-dimethylcyclopropanecarboxylate
Ausbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 314042,6-Di-tert-butyl-4-methylphenolKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

625 mg of (1R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid chloride was added under ice-water cooling to a mixed solution of 400 mg of (RS)-2-methyl-4-methylidene-3-ethylcyclopent-2-en-1-ol, 5 mg of 2,6-di-t-butyl-4-methylphenol and 274 mg of pyridine in 6 ml of toluene. The reaction was continued at an ambient temperature for eight hours. The reaction solution was added to a 5% citric acid solution under ice-water cooling, and extracted three times with diethyl ether. The combined ether layer was washed successively with a saturated sodium hydrogencarbonate solution and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the residue was subjected to silica gel column chromatography to yield 781 mg of (RS)-2-methyl-4-methylidene-3-ethyl-2-cyclopenten-1-yl (1R)-trans-3-(2,2-dichloro-vinyl)-2,2-dimethylcyclopropanecarboxylate (Compound No.5). Yield 82%.

Aufarbeitung

  1. extractionextracted three times with diethyl ether
  2. washThe combined ether layer was washed successively with a saturated sodium hydrogencarbonate solution
  3. dry with materiala saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. customAfter removal of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b9ef4c02bdbc4a6299cc4b6b2c6b5a55
Quelldatensatz
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05550258

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