Reaktionsgleichung
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:10](=[O:14])[CH2:11][CH2:12][CH:13]=1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:36]>C(Cl)Cl.CCCCCC>[Cl:36][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:10](=[O:14])[CH2:11][CH2:12][CH:13]=1Komponenten
Versuchsvorschrift
The following procedure was adopted from H. Hayaski et al., J. Amer. Chem. Soc., 95, 8749 (1972): To a solution containing 643 mg (3.28 mmol) of 2-(7-hydroxyheptyl)-2-cyclopentenone in 0.47 ml carbon tetrachloride at 35° (temperature of the external water bath), under argon, was added, dropwise over 1 hour, a solution containing 860 mg (3.28 mmol) triphenylphosphine in 3 ml of anhydrous methylene chloride. The yellow solution was stirred for an additional 4.0 hours at ca. 35° and overnight at reflux. The resultant brown residue was taken up in hot hexane and filtered through a sintered glass funnel containing a pad of Celite whereupon the filtrate was reduced in volume and column chromatographed using an 80% silicic acid-20% Celite column and benzene to 80% benzene-20% ethyl acetate in a gradient elution (5 ml fractions). Thus 2-(7-chloroheptyl)-2-cyclopentenone was obtained (20.2 mg) as a pale orange oil.
Aufarbeitung
- additionwas added, dropwise over 1 hour
- temperatureat reflux
- filtrationfiltered through a sintered glass funnel
- additioncontaining a pad of Celite whereupon the filtrate
- customchromatographed
- washin a gradient elution (5 ml fractions)
Quellen und Nachweise
- ORD-Eintrag
- ord-19a365b245904985928424d769b46765
- Quelldatensatz
- uspto-grants-1979_10
- Patentnummer
- US04171331
Verknüpfte Notizen
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