Water → [1-(2-Methyl-1,3-dioxolan-2-yl)cyclopropyl]methanol

HRID 1790878Notes

Reaction equation

HRID 1790878 reaction equation
C[O:2][C:3]([C:5]1([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1)=O.CC(C[AlH]CC(C)C)C.C(O)(C)C.O>C1(C)C=CC=CC=1>[CH3:13][C:8]1([C:5]2([CH2:3][OH:2])[CH2:7][CH2:6]2)[O:9][CH2:10][CH2:11][O:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 14487Diisobutylaluminum hydrideHCID 18725787HCID 18725787, compound

Product 1

HCID 22042312[1-(2-Methyl-1,3-dioxolan-2-yl)cyclopropyl]methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

11.2 g of 5 is dissolved in 150 ml of toluene and cooled under nitrogen to 0° C. 125 ml of DIBAH solution (1.2 M in toluene) is now slowly added in drops and stirred for 2 more hours. Then, 1.25 ml of isopropanol and 25 ml of water are added in drops and stirred overnight. The precipitate is filtered off, the filtrate is concentrated by evaporation and chromatographed on silica gel with ethyl acetate/hexane, whereby 9.1 of title compound 6 accumulates as a colorless oil.

Workup

  1. stirringstirred overnight
  2. filtrationThe precipitate is filtered off
  3. concentrationthe filtrate is concentrated by evaporation
  4. customchromatographed on silica gel with ethyl acetate/hexane, whereby 9.1 of title compound 6 accumulates as a colorless oil

Sources & evidence

ORD record
ord-defb7654daa34a208c68c11dbb800b7a
Source dataset
uspto-grants-2006_07
Patent number
US07071344B1

Reaction notes

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