تفاعل #166100

معادلة التفاعل

vinylmagnesium bromide

(2R)-2-benzhydryl-oxirane

23a

(2R)-2-benzhydryl-oxirane

→

(2S)-1,1-diphenyl-pent-4-ene-2-ol

المردود 70.5%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىquenched with saturated NH4Cl solution
2. 2
   استخلاصThe aqueous phase was extracted with ethyl acetate (3×30 ml)
3. 3
   غسيلThe combined organic phase was washed with brine
4. 4
   تجفيفdried over anhydrous Na2SO4
5. 5
   أخرىThe solvent was removed
6. 6
   أخرىthe residue was purified by flash chromatography on silica gel (Hexane/Ethyl Ether=4:1)

الإجراء التجريبي

(2R)-2-benzhydryl-oxirane (0.5 g, 2.38 mmol) 23a was dissolved in dry THF (5 ml) and was added into a dry THF solution at −78° C. containing CuI (0.045 g, 0.24 mmol) and vinylmagnesium bromide (5.95 ml of 1.0M solution in THF, 5.95 mmol). The reaction mixture was stirred and allowed to reach room temperature over a period of 2 h, and then quenched with saturated NH4Cl solution. The aqueous phase was extracted with ethyl acetate (3×30 ml). The combined organic phase was washed with brine and dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by flash chromatography on silica gel (Hexane/Ethyl Ether=4:1) to give 0.4 g (2S)-1,1-diphenyl-pent-4-ene-2-ol (70%, [α]D=(−)25, c=1, MeOH).

المصدر