m-Chloroperbenzoic acid → HCID 86668660, compound

HRID 73638Notes

Reaction equation

HRID 73638 reaction equation
[CH2:1]1[CH:10]2[C:5](=[CH:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][O:2]1.C1C=C(Cl)C=C(C(OO)=[O:19])C=1>C(Cl)Cl>[O:19]1[CH:6]2[C:5]31[CH:10]([CH2:9][CH2:8][CH2:7]2)[CH2:1][O:2][CH2:3][CH2:4]3

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66579282HCID 66579282, compound

Product 1

HCID 86668660HCID 86668660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3,4,6,7,8,8a-hexahydro-1H-isochromene (0.120 g, 0.868 mmol) in CH2Cl2 (6 mL) at 0° C. was added MCPBA (˜77%, 0.300 g, 1.30 mmol). The mixture was stirred at rt for 1 hr. It was quenched with sat'd. aq. sodium sulfite. The mixture was diluted with CH2Cl2 and said. aq. NaHCO3 then extracted with CH2Cl2. The combined organics were dried (anhd. Na2—SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound.

Workup

  1. customIt was quenched with sat'd
  2. additionThe mixture was diluted with CH2Cl2
  3. extractionaq. NaHCO3 then extracted with CH2Cl2
  4. dry with materialThe combined organics were dried (anhd. Na2—SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d8298d94d89a4f68b4c53b0a5621691a
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

Loading…