Sodium Chloride → (2S,3R)-1,2-Epoxy-2-(2,4-difluorophenyl)butan-3-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of diethyl L-(+)-tartrate (4.86 g, 0.0236 mole) in 940 ml of dry CH2Cl2 were added 12 g of activated 3A° molecular sieve powder and cooled the mixture to -5° C. Added a solution of titanium (IV) isopropoxide (14.4 g, .0506 mole) in 76 ml of CH2Cl2 followed by t-butyl hydroperoxide (22.4 g, 0.248 mole) in 150 ml of CH2Cl2 and continue to stir at -5° C. for 25 minutes. To this mixture, a solution of compound 6b, (2R)-3-(2,4-Difluorophenyl)-3-buten-2-ol, (15 g, 0.0815 moles) in 76 ml of CH2Cl2 was added and stirred for 12 hours at 5° C. Cooled the reaction mixture to -40° C., added 4(0 ml of 30% aq. NaOH solution saturated with NaCl and the mixture was allowed to warm to 10° C. Added 40 g of MgSO4, 12 g of celite and continued to stir at 10° C. for 30 minutes. The mixture was suction-filtered over celite. To the filtrate 560 ml of toluene, 450 ml of ether were added and insoluble material removed by filtration. The filtrate was evaporated in vacuo, the residue was dissolved in 400 ml of ether and suction filtered to remove the insoluble material. The filtrate was passed through a bed of silica gel and washed the pad of silica gel with 40 ml of ether. The filtrate was concentrated under reduced pressure to give yellow oil, which was chromatographed on silica gel. Elution with CHCl3 gave title compound 7c as oil (11.9 g, 73%).

Provenance & Evidence