m-Chloroperbenzoic acid → HCID 59568709, compound

HRID 1187088Notes

Reaction equation

HRID 1187088 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-451f412d27b749bf8fdd5cd1f34dbcac
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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