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

Participants

Reaction Steps

A flame-dried 100 mL round bottom 3-necked (RB3N) flask (note 1) filled with thermometer, stopcock, septum, and stirbar was purged with argon, charged with 4 A molecular sieves (300 mg; note 2) and 30 mL of dichloromethane (note 3), and cooled to -22° (30% ethylene glycol/water/dry ice). R,R-(+)-diethyl tartrate (97 mg; 47 mmol; note 4) and titanium(IV)isopropoxide (91 mg; 0.32 mmol; note 5) were added, and the mixture was stirred at -22±2° for 10 min. t-Butyl hydroperoxide (2.2 mL of a 5.8M dichloromethane solution; note 6) was added, and the mixture was stirred at -22±2° for 30 min. A solution of trans-2-decen-1-ol (1.00 g; 6.4 mmol; note 7) in dichloromethane, was then added. The mixture was stirred under argon at -22±2° until analysis (note 8) indicated >95% reaction (2.5 hr).

Provenance & Evidence