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

HRID 847443Notes

Reaction equation

HRID 847443 reaction equation
[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

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 14721902HCID 14721902, compound3×HCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2921a209b67c4970b9ffdfd1205656f3
Source dataset
uspto-grants-1992_08
Patent number
US05142061

Reaction notes

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