m-Chloroperbenzoic acid → HCID 86692801, compound

HRID 1466733Notes

Reaction equation

HRID 1466733 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9]/[CH:10]=[C:11](\[CH3:23])/[CH2:12][CH2:13]/[CH:14]=[C:15](\[CH3:22])/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH:6]=[C:5]([CH3:24])[CH:4]=1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9]/[CH:10]=[C:11](\[CH3:23])/[CH2:12][CH2:13]/[CH:14]=[C:15](\[CH3:22])/[CH2:16][CH2:17][CH:18]2[O:33][C:19]2([CH3:20])[CH3:21])[CH:6]=[C:5]([CH3:24])[CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66766023HCID 66766023, compound

Product 1

HCID 86692801HCID 86692801, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 24 (488.2 mg, 1.5 mmol) in 12 mL of dry CH2Cl2 at 0° C. was added a solution of MCPBA (403.4 mg, 1.80 mmol in 4 mL of CH2Cl2), the reaction mixture was stirred at 0° C. for 1 hr and then quenched with saturated aqueous NaHCO3 (50 mL). Et2O (3×50 mL) was then added, and the organic layer was washed with saturated aqueous NaHCO3, water, and brine, and dried with MgSO4 and concentrated to give a crude product. The crude product was passed through a silica gel column (hexanes/EtOAc 80:1, 40:1, 20:1) to give the pure epoxide 25 (104 mg: yield 20%) as a colorless oil.

Workup

  1. customquenched with saturated aqueous NaHCO3 (50 mL)
  2. additionEt2O (3×50 mL) was then added
  3. washthe organic layer was washed with saturated aqueous NaHCO3, water, and brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customto give a crude product

Sources & evidence

ORD record
ord-5cd745230f16451da89bf64edf0df283
Source dataset
uspto-grants-2015_04
Patent number
US09000050B2

Reaction notes

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