m-Chloroperbenzoic acid → HCID 59568716, compound

HRID 1187079Notes

Reaction equation

HRID 1187079 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH2:14])[C:5]([CH3:12])=[C:6]2[C:10]=1[C:9](=[O:11])[O:8][CH2:7]2.C1C=C(Cl)C=C(C(OO)=[O:23])C=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:14][O:23]2)[C:5]([CH3:12])=[C:6]2[C:10]=1[C:9](=[O:11])[O:8][CH2:7]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66643889HCID 66643889, compound

Product 1

HCID 59568716HCID 59568716, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7-fluoro-4-methyl-5-vinyl-3H-isobenzofuran-1-one (420 mg, 1.71 mmol) in 10 mL of DCM was slowly added mCPBA (741 mg, 85% purity, 3.43 mmol) in 10 mL of DCM at 0° C. After warming to room temperature, the mixture was stirred overnight. The mixture was washed with aqueous Na2SO3 until KI paper didn't change color. The organic layers was washed with brine and then concentrated. The residue was purified by column chromatography to give product 7-fluoro-4-methyl-5-oxiranyl-3H-isobenzofuran-1-one. The enantiomers of the product were resolved via SFC (Column: Chiralpak AD-H 250*4.6 mm ID, 5 um; Mobile phase: methanol (0.05% DEA) in CO2 from 5% to 40%; Flow rate: 2.35 mL/min; Wavelength: 220 nm). MS m/z 209 (M+1)−.

Workup

  1. customat 0° C
  2. washThe mixture was washed with aqueous Na2SO3 until KI paper didn't change color
  3. washThe organic layers was washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e6e7cc070a06456a8289b699186f4304
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

Loading…