Thionyl Chloride → 2-{4-[Chloro(cyclohexyl)methyl]-5-methylfuran-2-yl}-5-fluoropyridine
Reaction equation
[CH:1]1([CH:7]([C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=3)[O:11][C:10]=2[CH3:21])O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[Cl:24][CH:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=2)[O:11][C:10]=1[CH3:21]Participants
4
Procedure
To a solution of cyclohexyl[5-(5-fluoropyridin-2-yl)-2-methylfuran-3-yl]methanol (0.7 g) in toluene (10 mL) was added thionyl chloride (0.3 mL), and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure to give the title compound (0.7 g, 100%) as a yellow crystal.