(2-tert-Butyloxiran-2-yl)methanol → (2R)-2,3,3-Trimethylbutane-1,2-diol
Reaction equation
[CH3:1][C:2]([C:5]1([CH2:8][OH:9])[CH2:7][O:6]1)([CH3:4])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH3:7][C@@:5]([OH:6])([C:2]([CH3:4])([CH3:3])[CH3:1])[CH2:8][OH:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-(1,1-dimethylethyl)-2-oxiranemethanol (2.3 g, 17.7 mmol) in ethyl ether (10 ml) was added to a suspension of lithium aluminum hydride (1.477 g, 38.9 mmol) in ethyl ether (100 ml) at -5° C. and stirred at room temperature for 30 minutes. The mixture was cooled to 0° C., quenched with 10% aqueous sulfuric acid saturated with sodium sulfate. The aqueous layer was extracted with ethyl acetate and the combined extracts were washed with saturated sodium bicarbonate and brine and dried (magnesium sulfate). Concentration in vacuo followed by recrystallization from hexane gave 1.5 g of (R)-2,3,3-trimethyl-1,2-butanediol as a white solid.