3-(2,2-Dibromoethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride → HCID 20032126, Verbindung

HRID 231840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 231840
C(N1C2[C:7](=[CH:8][CH:9]=CC=2)[C:6]([CH:13]([OH:15])[CH3:14])=[C:5]1[C:16](F)(F)F)C#C.[Br:20][C:21]([Br:31])=[CH:22][CH:23]1[CH:25]([C:26](Cl)=[O:27])[C:24]1(C)C>N1C=CC=CC=1>[CH3:16][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH:22]([O:15][CH:13]([CH3:6])[CH3:14])([CH3:23])[CH3:21].[Br:31][C:21]([Br:20])=[CH:22][CH:23]1[CH:25]([C:26]([O-:27])=[O:15])[CH2:24]1

Komponenten

5

Edukt 2

HCID 129405823-(2,2-Dibromoethenyl)-2,2-dimethylcyclopropane-1-carbonyl chlorideHCID 88619781(RS) [1-(2-propynyl)-2-trifluoromethyl-(1H)-indol-3-yl]-ethanol

Produkt 2

HCID 20032126HCID 20032126, VerbindungHCID 21881879Diisopropylether hexane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

0.82 g of 1 (RS) [1-(2-propynyl)-2-trifluoromethyl-(1H)-indol-3-yl]-ethanol and 20 ml of 3-(2,2-dibromoethenyl)-2,2-dimethyl-cyclopropane-carboxylic acid chloride were mixed together at ambient temperature under an inert atmosphere, and 0.3 ml of pyridine were added. After stirring for 18 hours, the solvents were evaporated under reduced pressure to obtain 3.15 g of crude product which was purified by chromatography over silica (eluent: hexane-ethyl acetate 9-1 then hexane-isopropyl ether 9-1) to obtain 1(RS) [1-(2-propynyl)-2-trifluoromethyl-)1H)-indol-3-yl]-ethyl 1R,cis 2,2-dimethyl [3-(2,2-dibromoethenyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =-30.5°±1.6° (c=0.6% in toluene).

Aufarbeitung

  1. additionwere added
  2. customthe solvents were evaporated under reduced pressure
  3. customto obtain 3.15 g of crude product which
  4. customwas purified by chromatography over silica (eluent

Quellen und Nachweise

ORD-Eintrag
ord-0eb7d25190ac4e4fb8a88d52d2ed4394
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04849443

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