m-Chloroperbenzoic acid → 2,3-Epoxy-[4-(tert-butoxycarbonyl)phenoxy]butane

HRID 584152Notes

Reaction equation

[C:1]([O:5][C:6]([C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13]/[CH:14]=[CH:15]/[CH3:16])=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:24]>ClCCl.C1(C)C=CC=CC=1>[O:24]1[CH:14]([CH2:13][O:12][C:11]2[CH:17]=[CH:18][C:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[CH:9][CH:10]=2)[CH:15]1[CH3:16]

Participants

Conditions

Temperature: 22 °C

Procedure

A solution of trans-4-[4-(tert-butoxycarbonyl)phenoxy]-2-butene (3.10 g, 12.48 mmol) in dry dichloromethane (50 ml) was treated at 22° C. with 3-chloroperoxybenzoic acid (4.30 g, 24.9 mmol) and the resulting mixture was stirred at 22° C. for 18 hours. The mixture was then diluted with toluene, washed with 5% sodium thiosulfate, saturated sodium bicarbonate and brine. After drying (sodium sulfate), evaporation of the solvent gave an oil that was chromatographed on silica gel. Elution with a mixture of toluene and ethyl acetate (95:5) gave 3.16 g (96%) of the title material as an oil which solidified upon standing: bp 85-90° C./0.05 torr (bulb to bulb, air bath temperature); mp 47-48° C.

Workup

washwashed with 5% sodium thiosulfate, saturated sodium bicarbonate and brine
customAfter drying
custom(sodium sulfate), evaporation of the solvent
customgave an oil that
customwas chromatographed on silica gel
washElution
additionwith a mixture of toluene and ethyl acetate (95:5)

Sources & evidence

ORD record: ord-d67d261053a94aff9cf5845ffc441e9f
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924391B2

Reaction notes

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