Triethyl phosphite → Diethyl [(2-ethyl-5-methyl-1,3-thiazol-4-yl)methyl]phosphonate
Reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH2:9][CH3:10])[S:6][C:7]=1[CH3:8].[P:11]([O:18]CC)([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]>>[CH2:9]([C:5]1[S:6][C:7]([CH3:8])=[C:3]([CH2:2][P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])[N:4]=1)[CH3:10]Participants
3
Conditions
- Temperature
- 160 °C
Procedure
A mixture of 4-chloromethyl-2-ethyl-5-methyl-1,3-thiazole (3.2 g) and triethyl phosphite (6.7 g) was stirred at 160° C. for 16 hrs. Excess triethyl phosphite was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:2-1:1, v/v) to give diethyl [(2-ethyl-5-methyl-1,3-thiazol-4-yl)methyl]phosphonate as a colorless oil (4.9 g, yield 97%).