(2-tert-Butyloxiran-2-yl)methanol → (2R)-2,3,3-Trimethylbutane-1,2-diol

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.

1. temperatureThe mixture was cooled to 0° C.
2. customquenched with 10% aqueous sulfuric acid saturated with sodium sulfate
3. extractionThe aqueous layer was extracted with ethyl acetate
4. washthe combined extracts were washed with saturated sodium bicarbonate and brine
5. dry with materialdried (magnesium sulfate)
6. concentrationConcentration in vacuo
7. customfollowed by recrystallization from hexane

ORD record

ord-c30e43812ad4457eb1d9192623ee6268

Source dataset

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05492910