تفاعل #358640

معادلة التفاعل

SOCl2

(Z)-4-amino-1,1,1-trifluorobut-3-en-2-one

methyl acetoacetate

(Z)-4-amino-1,1,1-trifluorobut-3-en-2-one

methyl 3-oxopentanoate

3-(chloromethyl)-2-methyl-6-(trifluoromethyl)pyridine

TFA

(2-ethyl-6-(trifluoromethyl)pyridin-3-yl)methanol

lithium aluminum hydride

methyl 2-ethyl-6-(trifluoromethyl)nicotinate

→

title compound

3-(chloromethyl)-2-ethyl-6-(trifluoromethyl)pyridine

ظروف التفاعل

الإجراء التجريبي

The title compound was prepared from (Z)-4-amino-1,1,1-trifluorobut-3-en-2-one and methyl 3-oxopentanoate analogously to the way 3-(chloromethyl)-2-methyl-6-(trifluoromethyl)pyridine was prepared from (Z)-4-amino-1,1,1-trifluorobut-3-en-2-one and methyl acetoacetate in three steps: 1. TFA-mediated cyclocondensation to methyl 2-ethyl-6-(trifluoromethyl)nicotinate (HPLC/MS: retention time=3.2 min, [M+H]30 =234); 2. reduction with lithium aluminum hydride to (2-ethyl-6-(trifluoromethyl)pyridin-3-yl)methanol (HPLC/MS: retention time=2.4 min, [M+H]+=206); and 3. reaction with SOCl2 to afford the title compound (HPLC/MS: retention time=3.3 min, [M+H]30 =224).

المصدر