tert-Butyl hydroperoxide → (2S,3S)-3-heptyloxiranemethanol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A solution of Ti(O-i-Pr)4 (0.6 ml, 0.57g, 2.0 mmole) and (+)-DET (0.45 g, 2.2 mmole) in CH2Cl2 (10 ml) was cooled to -20° C. in a CCl4 -Dry Ice bath. trans-1-Decen-1-ol (0.312 g, 2.0 mmole) in CH2Cl2 (1 ml) was added followed by addition of TBHP (4.0 mmole in toluene). The resulting solution was stirred at -20° C. for 2.25 hr and then was quenched by stirring with sat'd aq. Na2SO4 (2 ml) and ether (80 ml) for one hour. The mixture was filtered through Celite, dried (MgSO4), filtered, and concentrated. The crude product was chromatographed over silica gel (11.5 g, 10% acetone-hexane, 6 ml fractions) giving 0.244 g of 35 (1.42 mmole, 71%) which contained traces of a more polar impurity and a less polar impurity. This material was crystalline.

Herkunft & Nachweise