m-Chloroperbenzoic acid → HCID 86758724, compound

HRID 2300410Notes

Reaction equation

HRID 2300410 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]2[CH:3]1[CH:4]2[C:8]([O:10][CH2:11][CH3:12])=[O:9].ClC1C=CC=C(C(OO)=[O:21])C=1>ClCCl>[O:21]=[C:2]1[O:1][CH2:7][CH2:6][CH:5]2[CH:3]1[CH:4]2[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 565357Ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate

Product 1

HCID 86758724HCID 86758724, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of ethyl (1SR,5RS,6SR)-2-oxo-bicyclo[3.1.0]hexane-6-carboxylate (34.8 g, 207.2 mmol) in dichloromethane (300 mL), 70% m-chloroperbenzoic acid (51.1 g, 207.2 mmol) was added and refluxed overnight. The following day, additional 70% m-chloroperbenzoic acid (51.1 g, 207.2 mmol) was added and reflux continued for 15 hours. After that time, the mixture was diluted with dichloromethane (200 mL), filtered and washed with 10% Na2SO3 (2×200 mL) and with a saturated aqueous solution of sodium bicarbonate (2×200 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by column chromatography using ethyl acetate and hexane 1:2 as eluent to give 22.89 g (60% yield) of ethyl (1SR,6SR,7SR)-2-oxo-3-oxa-bicyclo[4.1.0]heptane-7-carboxylate as a colorless oil.

Workup

  1. temperaturerefluxed overnight
  2. temperaturereflux
  3. filtrationfiltered
  4. washwashed with 10% Na2SO3 (2×200 mL) and with a saturated aqueous solution of sodium bicarbonate (2×200 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2ab35d643e2b4a848d699acab3728e18
Source dataset
uspto-grants-2002_12
Patent number
US06498180B1

Reaction notes

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