Water → 1-(4-Chlorobenzyl)-1,2-epoxy-3,3-dimethyl-2-hydroxymethylcyclopentane

HRID 847443노트

반응식

HRID 847443 반응식
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][C:7]23[O:18][C:8]2([C:14](OC)=[O:15])[C:9]([CH3:13])([CH3:12])[CH2:10][CH2:11]3)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][C:7]23[O:18][C:8]2([CH2:14][OH:15])[C:9]([CH3:13])([CH3:12])[CH2:10][CH2:11]3)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 14721902HCID 14721902, 화합물3회HCID 21226445Aluminium lithium hydride

생성물 1

HCID 190207391-(4-Chlorobenzyl)-1,2-epoxy-3,3-dimethyl-2-hydroxymethylcyclopentane수율 99.1%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

10.7 g (36.3 mmols) 1-(4-chlorobenzyl)-1,2-epoxy-3,3-dimethyl-2-methoxycarbonylcyclopentane prepared as described in (g) were dissolved in diethyl ether and the resulting solution was then added to a slurry of 1.5 g (36.6 mmols) lithium aluminium hydride in 50 ml diethyl ether at a rate such that reflux of the reaction mixture was maintained. Heating was continued for 5 minutes after the last addition of 1-(4-chlorobenzyl)-1,2-epoxy-3,3-dimethyl-2 -methoxycarbonylcyclopentane solution. 1.25 ml water were then added, followed by 1.25 ml 15% aqueous sodium hydroxide solution and a further 4 ml water. The solid was filtered off and the filtrate was then dried over anhydrous magnesium sulphate and flashed to give a clear oil which crystallised on cooling to give 9.6 g 1-(4-chlorobenzyl)-1,2-epoxy-3,3-dimethyl-2-hydroxymethylcyclopentane as a solid. m.pt. 36°-38° C., which can be reduced to 1-(4-chlorobenzyl)-3,3-dimethyl-2-hydroxy-2-hydroxymethylcyclopentane in a conventional method.

후처리

  1. temperaturethat reflux of the reaction mixture
  2. temperaturewas maintained
  3. temperatureHeating
  4. filtrationThe solid was filtered off
  5. dry with materialthe filtrate was then dried over anhydrous magnesium sulphate
  6. customto give a clear oil which
  7. customcrystallised
  8. temperatureon cooling

출처 및 근거

ORD 기록
ord-2921a209b67c4970b9ffdfd1205656f3
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05142061

반응 노트

불러오는 중…