Water → 75658-83-2

HRID 1441081Notes

Reaction equation

HRID 1441081 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[CH:12]([OH:14])[CH3:13].[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[CH2:12][OH:14]

Participants

5

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 3776IsopropanolHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 1019770775658-83-2

Conditions

Temperature
0 °C

Procedure

46 ml of a 1.2 molar solution of diisobutylaluminum hydride in toluene is instilled in a solution of 2.8 g of 2-hydroxymethyl-cyclobutanecarboxylic acid lactone (C. C. Schroff et al., J. Org. Chem. 36, 3356 (1971)) in 70 ml of toluene at 0° C. under argon and stirred for 50 minutes at 0° C. Then, 20 ml of 2-propanol and 23 ml of water are instilled, stirred for 2 hours at 22° C. filtered washed with dichloromethane and concentrated by evaporation in a vacuum. The residue is purified by chromatography on silica gel. With ethyl acetate/hexane (4+1), 2.1 g of cis-1,2-dihydroxymethyl-cyclopentane is obtained as colorless liquid.

Workup

  1. stirringstirred for 2 hours at 22° C.
  2. filtrationfiltered
  3. washwashed with dichloromethane
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-2982204ae5494b939bac309524048ee4
Source dataset
uspto-grants-1996_03
Patent number
US05502075

Reaction notes

Loading…