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

HRID 584152노트

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HRID 584152 반응식
[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]

참가 물질

5

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 22345517trans-4-[4-(Tert-butoxycarbonyl)phenoxy]-2-butene

생성물 1

HCID 223455372,3-Epoxy-[4-(tert-butoxycarbonyl)phenoxy]butane수율 96%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

반응 조건

온도
22 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d67d261053a94aff9cf5845ffc441e9f
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924391B2

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