((2S,3R)-3-Undecyloxiran-2-yl)methanol → (R)-1,3-dihydroxytetradecane

Participants

Reaction Conditions

Reaction Steps

To a solution of epoxide 8 (9.00 g, 40 mmol) in tetrahydrofuran (80 mL) at -20° C. was added a solution of Red-Al (40 mL, 3M) and the reaction temperature was slowly raised to 0° C. and subsequently to room temperature and stirred for 12 h. After completion of the reaction (TLC), the excess of Red-Al was quenched with methanol (10 mL) and poured in to a conical flask containing ethyl acetate (400 mL) and rochelle salt solution (100 mL) and stirred for 2 h until clear separation of two layers occurred. The organic layer was separated, dried and concentrated to give the diol 9 as a colorless solid (8.1 g, 89%). m.p. 59°-60° C.

Provenance & Evidence