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

HRID 847443ノート

反応式

HRID 847443 の反応式
[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

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 14721902HCID 14721902、化合物3 回HCID 21226445Aluminium lithium hydride

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2921a209b67c4970b9ffdfd1205656f3
出典データセット
uspto-grants-1992_08
特許番号
US05142061

反応ノート

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