Trifluoroacetic acid → 3-(Chloromethyl)-2-ethyl-6-(trifluoromethyl)pyridine

HRID 271458

Reaktionsgleichung

Reaktionsgleichung von HRID 271458
N/[CH:2]=[CH:3]\[C:4](=O)[C:5]([F:8])([F:7])[F:6].O=[C:11](CC)CC(OC)=O.[Cl:19][CH2:20][C:21]1[C:22]([CH3:31])=[N:23]C(C(F)(F)F)=CC=1.C(OC)(=O)CC(C)=O.C(O)(C(F)(F)F)=O.C(C1N=C(C(F)(F)F)C=CC=1C(OC)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C1C(CO)=CC=C(C(F)(F)F)N=1)C.O=S(Cl)Cl>>[Cl:19][CH2:20][C:21]1[C:22]([CH2:31][CH3:11])=[N:23][C:4]([C:5]([F:8])([F:7])[F:6])=[CH:3][CH:2]=1

Komponenten

10

Edukt 9

HCID 6422Trifluoroacetic acidHCID 7757Methyl acetoacetateHCID 24386Thionyl ChlorideHCID 121699Methyl 3-oxovalerateHCID 11116141(Z)-4-amino-1,1,1-trifluorobut-3-en-2-one2×HCID 21226445Aluminium lithium hydrideHCID 598348153-(Chloromethyl)-2-methyl-6-(trifluoromethyl)pyridineHCID 69056451Methyl 2-ethyl-6-(trifluoromethyl)nicotinateHCID 69064910(2-Ethyl-6-(trifluoromethyl)pyridin-3-yl)methanol

Produkt 1

HCID 598348093-(Chloromethyl)-2-ethyl-6-(trifluoromethyl)pyridine

Versuchsvorschrift

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).

Quellen und Nachweise

ORD-Eintrag
ord-fb142cb6d63f40f39f915d9ae9d9fddd
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452892B2

Verknüpfte Notizen

Wird geladen…