Water → 1-Phenyl-7-oxabicyclo[4.1.0]heptane

HRID 1108006

Reaction equation

HRID 1108006 reaction equation
[C:1]1([C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(O)=[O:14].[Na+].OOS([O-])=O.[K+].O>C(#N)C.O>[C:1]1([C:7]23[O:14][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 130431-PhenylcyclohexeneHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 1001931-Phenyl-7-oxabicyclo[4.1.0]heptaneYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of phenyl cyclohexene (79 mg, 0.5 mmol) in a mixture of acetonitrile (4.5 ml) and water (2 drops) were added first finely crushed NaHCO3 (168 mg, 2 mmol) and oxone (307 mg, 0.5 mmol) then the catalyst (0.05 mmol). The resulting yellow suspension was allowed to react at RT, under good stirring. TLC was used to follow the reaction which indicated that the reaction was finished in 2 h. Water (3 ml) was added to the reaction mixture followed by extraction into methylene dichloride. The organic extracts were combined and dried over anhydrous sodium sulphate. Concentration on a rotary evaporator gave a material which was purified on a column using 2% ethyl acetate:petrol mixture as eluent to give the desired compound as a colourless oil. (72 mg, 83% yield, 70% e.e).

Workup

  1. customto react at RT, under good stirring
  2. customthe reaction which
  3. extractionfollowed by extraction into methylene dichloride
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationConcentration
  6. customon a rotary evaporator
  7. customgave a material which
  8. customwas purified on a column

Sources & evidence

ORD record
ord-94395df33f7f4c38bcdf1e38099dd4be
Source dataset
uspto-grants-2000_05
Patent number
US06063920

Linked notes

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