Reaktion #2493682

Reaktionsgleichung

6,6-Dimethyl-3-phenylselanyl-bicyclo[3.1.1]heptan-2-one

pyridine

H2O2

→

final product

6,6-Dimethylbicyclo[3.1.1]hept-3-en-2-one

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe temperature of the flask was dropped to 0° C
2. 2
   workup.STIRRINGNext, the reaction was stirred at room temperature overnight
3. 3
   Waschenthe mixture was washed with water, NaHSO3, and CuSO4
4. 4
   Trocknendried with NaSO4
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe concentrate was purified via column chromatography

Vorschrift

6,6-Dimethyl-3-phenylselanyl-bicyclo[3.1.1]heptan-2-one, pyridine (8.71 mL), and methylene chloride (650 μL) were combined in a round bottom flask. The temperature of the flask was dropped to 0° C. 67.5 μL of H2O2 was added to the flask and allowed to stir at room temperature for 5 hours at 0° C. Next, the reaction was stirred at room temperature overnight. 5 mL of methylene chloride was added to the solution, and the mixture was washed with water, NaHSO3, and CuSO4, dried with NaSO4, and concentrated. The concentrate was purified via column chromatography to afford final product (70:30, Hexane: EtOAc). 1H NMR (500 MHz, CDCl3): δ (ppm) 1.485 (s, 3H), 1.517 (s, 3H), 2.145 (d, 3H), 2.2.616 (m, 1H), 2.724 (m, 1H), 2.849 (m, 1H), 5.958 (d, 1H), 7.526 (dd, 1H). (ESI, Pos) m/z 159.0 (M+23).

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