m-Chloroperbenzoic acid → HCID 86668658, compound

HRID 73631Notes

Reaction equation

HRID 73631 reaction equation
[CH2:1]1[C:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH: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[C@@:10]23[C@H:5]([CH2:4][CH2:3][O:2][CH2:1]2)[CH2:6][CH2:7][CH2:8][CH:9]13

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 536948903,4,4a,5,6,7-hexahydro-1H-isochromene

Product 1

HCID 86668658HCID 86668658, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3,4,4a,5,6,7-hexahydro-1H-isochromene (0.410 g, 2.97 mmol) in CH2Cl2 (10 mL) at 0° C. was added MCPBA (˜77%, 1.24 g, 445 mmol). The mixture was stirred at rt for 3 hr. It was quenched with sat'd aq. sodium sulfite. The mixture was diluted with CH2Cl2 and sat'd. aq. NaHCO3 then extracted 3× with CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 4.03-4.10 (m, 1H), 3.86 (d, 1H, J=12.0 Hz), 3.54-3.62 (m, 1H), 3.34 (d, 1H, J=12.0 Hz), 3.03 (d, 1H, J=4.4 Hz), 1.70-1.98 (m, 3H), 1.52-1.65 (m, 3H), 1.17-1.34 (m, 3H).

Workup

  1. customIt was quenched with sat'd aq. sodium sulfite
  2. additionThe mixture was diluted with CH2Cl2
  3. extractionaq. NaHCO3 then extracted 3× with CH2Cl2
  4. dry with materialThe combined organics were dried (anhd. Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2fbbad9f4c7e46888538a445300e167c
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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