m-Chloroperbenzoic acid → 6-Cyclopropyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one

HRID 1187083Notes

Reaction equation

HRID 1187083 reaction equation
[CH:1]1([C:4]2[C:5]([CH:14]=[CH2:15])=[CH:6][C:7]3[CH2:11][O:10][C:9](=[O:12])[C:8]=3[CH:13]=2)[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:24])C=1>ClCCl.C(=O)(O)[O-].[Na+]>[CH:1]1([C:4]2[C:5]([CH:14]3[CH2:15][O:24]3)=[CH:6][C:7]3[CH2:11][O:10][C:9](=[O:12])[C:8]=3[CH:13]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 666463936-Cyclopropyl-5-vinyl-2-benzofuran-1(3H)-one

Product 1

HCID 595686646-Cyclopropyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

6-Cyclopropyl-5-vinyl-2-benzofuran-1(3H)-one (0.45 g, 2.25 mmol) was dissolved in dichloromethane (10 mL) and treated with meta-chloro perbenzoic acid (1 g, 6.3 mmol) at 0° C. and stirred for 12 h. TLC indicated completion of the reaction; the mixture was diluted with saturated sodium bicarbonate solution and extracted with dichloromethane (2×). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The epoxide was purified by silica gel column chromatography (hexanes/EtOAc=1/1) to give 6-Cyclopropyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one. The oxirane was further resolved over a chiral column giving two isomers:

Workup

  1. customcompletion of the reaction
  2. extractionextracted with dichloromethane (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe epoxide was purified by silica gel column chromatography (hexanes/EtOAc=1/1)

Sources & evidence

ORD record
ord-26aaa0885d8d434e8cb1520b3ba18df4
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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