تفاعل #41340

معادلة التفاعل

1-bromo-4-(trifluoromethyl)benzene

N2-(tert-butoxycarbonyl)-N-methoxy-N-methyl-L-alaninamide

→

tert-Butyl {(1S)-1-methyl-2-oxo-2-[4-(trifluoromethyl)phenyl]ethyl}carbamate

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.WAITthe stirring was continued overnight at r.t
2. 2
   أخرىThen the reaction mixture was quenched with sat. aq. NH4Cl (20 ml)
3. 3
   workup.WAITwas continued for 30 min
4. 4
   أخرىThe layers were separated
5. 5
   استخلاصthe aqueous layer extracted with ethyl acetate (20 ml)
6. 6
   تجفيفThe combined organic extracts were dried over Na2SO4
7. 7
   أخرىthe solvent was evaporated
8. 8
   أخرىto give yellow partly crystalline product
9. 9
   أخرىPurification by flash chromatography on silica gel with n-heptane/ethyl acetate afforded colourless solid, 260 mg (82%)

الإجراء التجريبي

To a stirred mixture of isopropylmagnesium chloride-lithium chloride complex (14% wt 1 M solution, 726 mg, 5 mmol, 5 ml) and THF (5 ml) was added 1-bromo-4-(trifluoromethyl)benzene (1.125 g, 5 mmol) under argon. The stirring was continued at r.t. for 4 h. A solution of N2-(tert-butoxycarbonyl)-N-methoxy-N-methyl-L-alaninamide (232 mg, 1 mmol) in THF (10 ml) was added dropwise, and the stirring was continued overnight at r.t. Then the reaction mixture was quenched with sat. aq. NH4Cl (20 ml), and stirring was continued for 30 min. The layers were separated, the aqueous layer extracted with ethyl acetate (20 ml). The combined organic extracts were dried over Na2SO4, and the solvent was evaporated to give yellow partly crystalline product. Purification by flash chromatography on silica gel with n-heptane/ethyl acetate afforded colourless solid, 260 mg (82%).

المصدر