Allyl Alcohol → HCID 51674883, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of allyl alcohol (1.0 ml, 14.7 mmol) in chloroform (15.0 ml) was added 1.0 M diethylzinc in heptane (15.0 ml, 15.0 mmol) and stirred for 15 min under an atmosphere of nitrogen. A solution of (2R,3R)-diisopropyl 2,3-dihydroxysuccinate (2.7 ml, 12.7 mmol) was added to above mixture and stirred for 2 hours. Then another portion of 1.0 M diethylzinc in heptane (15.0 ml, 15.0 mmol) was added at 0° C. A solution of α-chloro-4-fluorobenzaldoxime (2.8 g, 16.1 mmol) in chloroform (15 ml) was added to the reaction mixture. After 3 hours, the reaction was quenched with saturated NH4Cl4, and the mixture extracted with CHCl3 (3×50 ml). The combined organic phase was washed with brine, dried over Mg2SO4, filtered, and concentrated under reduced pressure to yield a crude solid. Chromatography (1:98 to 10:90 MeOH:CH2Cl2) over silica gel yielded ((R)-3-(4-fluorophenyl)-4,5-dihydroisoxazol-5-yl)methanol, a compound of formula (22) as a white solid (2.34 g, 12.0 mmol).

Provenance & Evidence