Water → 75658-83-2

HRID 36378Notes

Reaction equation

HRID 36378 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH:11]([OH:14])([CH3:13])C.[OH2:15].[C:16]1(C)C=[CH:20][CH:19]=[CH:18][CH:17]=1>>[OH:15][CH2:20][C@@H:19]1[CH2:18][CH2:17][CH2:16][C@@H:13]1[CH2:11][OH:14]

Participants

5

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 3776IsopropanolHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 1019770775658-83-2

Conditions

Temperature
22 °C

Procedure

127 ml of a 1.2 molar solution of diisobutylaluminum hydride in toluene is instilled in a solution of 8.7 g of 2-hydroxymethyl-cyclopentanecarboxylic acid lactone (O. Caamano et al., Euro. J. Med. Chem. 22, 311 (1987)) in 127 ml of toluene at 0° C. under argon and stirred for 50 minutes at 0° C. Then, 25 ml of isopropanol and 63 ml of water are instilled, stirred for 2 hours at 22° C., filtered washed with methylene chloride and concentrated by evaporation in a vacuum. The residue is purified by chromatography on silica gel. With ethyl acetate/hexane (4+1), 7 g of cis-1,2-dihydroxymethyl-cyclopentane is obtained as colorless liquid.

Workup

  1. filtrationfiltered
  2. washwashed with methylene chloride
  3. concentrationconcentrated by evaporation in a vacuum
  4. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b4f15ebb95914a63b4dea292357e68b1
Source dataset
uspto-grants-1995_05
Patent number
US05414016

Reaction notes

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