m-Chloroperbenzoic acid → HCID 86647585, compound

HRID 1471397Notes

Reaction equation

HRID 1471397 reaction equation
[CH3:1][C:2]1[CH:3]([C:12]([O:14][CH3:15])=[O:13])[C:4]2([CH2:9][CH2:10][CH:11]=1)[CH2:8][CH2:7][CH2:6][CH2:5]2.C1C=C(Cl)C=C(C(OO)=[O:24])C=1>ClCCl>[CH3:1][C:2]12[O:24][CH:11]1[CH2:10][CH2:9][C:4]1([CH2:8][CH2:7][CH2:6][CH2:5]1)[CH:3]2[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68724110HCID 68724110, compound

Product 1

HCID 86647585HCID 86647585, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

At 5° C., a solution of methyl 7-methylspiro[4.5]dec-7-ene-6-carboxylate (13.5 g, 60 mmol, prepared as described in Example 25) in dichloromethane (150 ml) was treated with MCPBA (17.8 g, 72 mmol). The resulting mixture was stirred for 4 h at 20° C., filtered, and the organic phase was washed with water (100 ml), dried (MgSO4), concentrated, and gave crude methyl 1-methyl-7-oxaspiro[bicyclo[4.1.0]heptane-3,1′-cyclopentane]-2-carboxylate (13 g). Boiling point: 130° C. (0.08 mbar).

Workup

  1. filtrationfiltered
  2. washthe organic phase was washed with water (100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c935d46c03074a06a182f946ca26bb39
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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