m-Chloroperbenzoic acid → HCID 86668654, compound

HRID 73620Notes

Reaction equation

HRID 73620 reaction equation
[O:1]1[CH:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)=[CH:4][CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:19])C=1>C(Cl)Cl>[O:19]1[C@@:5]23[CH:10]([CH2:9][CH2:8][CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3][C@H:4]13

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66577517HCID 66577517, compound

Product 1

HCID 86668654HCID 86668654, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3,5,6,7,8,8a-hexahydro-2H-chromene (3.27 g, 23.66 mmol) in CH2Cl2 (75 mL) at 0° C. was added MCPBA (˜77%, 6.53 g, 28.4 mmol). The mixture was warmed to rt and stirred for 1 hr. The mixture was quenched with sat'd. aq. Na2SO3. The mixture was then partitioned between CH2Cl2 and sat'd. aq. NaHCO3. Extracted with CH2Cl2. The combined organics were dried, filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 3.85 (dd, 1H, J=7.8 Hz, 11.7 Hz), 3.54 (dd, 1H, J=4.6 Hz, 11.7 Hz), 3.31-3.38 (m, 1H), 3.19 (d, 1H, J=5.13 Hz), 2.15-2.24 (m, 1H), 1.75-1.97 (m, 4H), 1.52-1.72 (iii, 3H), 1.37-1.49 (m, 1H), 1.30-1.38 (m, 1H).

Workup

  1. customThe mixture was quenched with sat'd
  2. customThe mixture was then partitioned between CH2Cl2
  3. extractionExtracted with CH2Cl2
  4. customThe combined organics were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5af08c083cfd493fb38baa9bc8abc0e1
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

Loading…