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

HRID 2406500Notes

Reaction equation

HRID 2406500 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH:5]([Se]C1C=CC=CC=1)[C:6]2=[O:9].N1C=CC=CC=1.OO>C(Cl)Cl>[CH3:1][C:2]1([CH3:17])[CH:7]2[CH2:8][CH:3]1[CH:4]=[CH:5][C:6]2=[O:9]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 1049PyridineHCID 85300314HCID 85300314, compound

Product 1

HCID 1554776,6-Dimethylbicyclo[3.1.1]hept-3-en-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

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).

Workup

  1. additionThe temperature of the flask was dropped to 0° C
  2. stirringNext, the reaction was stirred at room temperature overnight
  3. washthe mixture was washed with water, NaHSO3, and CuSO4
  4. dry with materialdried with NaSO4
  5. concentrationconcentrated
  6. customThe concentrate was purified via column chromatography

Sources & evidence

ORD record
ord-053c9f6256e44491aef38d269cf33ef7
Source dataset
uspto-grants-2014_08
Patent number
US08809373B2

Reaction notes

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