m-Chloroperbenzoic acid → HCID 59568709, compound

HRID 1474346Notes

Reaction equation

HRID 1474346 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:12])[O:10][CH2:11][C:7]=2[CH:6]=[C:5]([CH:13]=[CH2:14])[CH:4]=1.ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:12])[O:10][CH2:11][C:7]=2[CH:6]=[C:5]([CH:13]2[CH2:14][O:23]2)[CH:4]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66643933HCID 66643933, compound

Product 1

HCID 59568709HCID 59568709, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 7-methoxy-5-vinyl-2-benzofuran-1(3H)-one in DCM (5 mL) was added meta-chloro perbenzoic acid (0.18 g, 1.05 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 DCM (2×). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The resulting epoxide was purified by silica gel column chromatography (hexanes/EtOAc=1/1) to give 7-methoxy-5-oxiran-2-yl-2-benzofuran-1(3H)-one. LC/MS: [(M+1)]+=207.

Workup

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

Sources & evidence

ORD record
ord-de34ef46fe8949ab91ba0cea630f6d32
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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