m-Chloroperbenzoic acid → HCID 86693879, compound

HRID 1186917Notes

Reaction equation

HRID 1186917 reaction equation
[C:1]([Si:5]([O:8][CH2:9][C@@H:10]1[C@@H:17]2[C@@H:13]([O:14][C:15]([CH3:19])([CH3:18])[O:16]2)[CH:12]=[CH:11]1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:28])C=1>ClCCl>[C:1]([Si:5]([O:8][CH2:9][C@@H:10]1[C@H:17]2[O:16][C:15]([CH3:19])([CH3:18])[O:14][C@H:13]2[C@@H:12]2[O:28][C@H:11]12)([CH3:7])[CH3:6])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 89762123HCID 89762123, compound

Product 1

HCID 86693879HCID 86693879, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound 9 (5.0 g, 17.5 mmol) in dichloromethane (40 mL) at room temperature was added portion wise m-CPBA (13.6 g, 78.9 mmol). Mixture was stirred at room temperature for 6 h, quenched with saturated NaHCO3 solution and the mixture was extracted with DCM (50 mL×2). The combined organic layers were washed with brine (40 mL×2) dried over Na2SO4. The solvent was removed under reduced pressure and residue was purified by silica gel column chromatography (3% EtOAc/Hexane) to give epoxide 10 (3.5 g, 66%) as an oil. [α]24D +58.19° (c 1.0, CHCl3); 1H NMR (500 MHz, CDCl3) δ 4.54-4.52 (m, 1H), 3.91-3.90 (m, 1H,), 3.73-3.69 (m, 1H), 3.59-3.55 (m, 3H), 2.316-2.311 (m, 1H), 1.38 (s, 3H), 1.22 (s, 3H), 0.83-0.82 (m, 9H), 0.006-0.000 (m, 6H); HR-MS Calcd. For (C15H28O4Si+H)+ 301.1757, found 301.1895.

Workup

  1. customquenched with saturated NaHCO3 solution
  2. extractionthe mixture was extracted with DCM (50 mL×2)
  3. washThe combined organic layers were washed with brine (40 mL×2)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure and residue
  6. customwas purified by silica gel column chromatography (3% EtOAc/Hexane)

Sources & evidence

ORD record
ord-500d445d605945cebb64ae8889ae3bd0
Source dataset
uspto-grants-2014_03
Patent number
US08673926B2

Reaction notes

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