Triphenylphosphine → HCID 86594336, compound

HRID 2361878Notes

Reaction equation

HRID 2361878 reaction equation
[CH2:1]1[O:12][C:4]2([CH:9]3CC[CH:5]2[CH2:6][CH2:7][CH2:8]3)[O:3][CH2:2]1.[O:13]=[O+][O-].C1(P([C:29]2[CH:34]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:2]1[O:3][C:4]2([CH2:5][CH:6]3[C:7](=[O:13])[CH:8]([CH2:34][CH2:29]3)[CH2:9]2)[O:12][CH2:1]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823Ozone2×HCID 13583530HCID 13583530, compound

Product 1

HCID 86594336HCID 86594336, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-methylenyl bicyclo[3,2,1]octan-8-one ethylene ketal (0.21 g, 1.15 mmol, 1.0 eq.) in CH2Cl2 (2 mL) at −78° C. was bubbled O3 until the reaction stayed blue (about 3 min). The O3 bubbling was stopped and the reaction mixture was stirred for 5 min at −78° C. The reaction was quenched by addition of triphenylphosphine (0.43 g, 1.4 eq.) and stirring at −78° C. for 10 minutes. The reaction mixture was allowed to warm at room temperature, stirred for 40 minutes and concentrated. The residue was purified by silica gel chromatography (10% to 15% EtOAc-hexanes) to give bicyclo[3,2,1]octane-3,8-dione 8-ethylene ketal as a colorless oil (0.08 g, 40%).

Workup

  1. custom(about 3 min)
  2. stirringstirring at −78° C. for 10 minutes
  3. temperatureto warm at room temperature
  4. stirringstirred for 40 minutes
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (10% to 15% EtOAc-hexanes)

Sources & evidence

ORD record
ord-fa0bd720f9bc478a803c31fafdea2632
Source dataset
uspto-grants-2014_04
Patent number
US08691814B2

Reaction notes

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