Dimethyl Sulfate → HCID 19849677, compound

Participants

Reaction Steps

The starting material was obtained as follows. Reaction of 1,2,3,4-tetrahydro-4-oxopyridine with 2 equivalents of allyl bromide and potassium carbonate in acetone under reflux for 15 hours gave, after purficiation by silica gel/EtOAc chromatography, 1,2,3,4,-tetrahydro-1-allyl-4-oxopyridine, nmr in CHCl3 :-2.5 tetrahydro-1-allyl4-oxopyridine, nmr in CHCl3 :-2.5 (t,2H); 3.46(t,2H); 3.8(d,2H); 5.0(d,1H); 5.24(m,1H); 5.4(m,1H); 5.4(m,1H); 5.8(m,1H); 7.06(d,1H). Reaction of this compound with dimethylsulphate at ambient temperature for 18 hours gave 1-allyl-2,3-dihydro-4-methoxypyridineium methyl sulphate. nmr in CDCl3 :-2.86(t,2H); 3.68(s,3H); 3.94(t,2H0; 3.96(s,3H); 4.5 (d,2H); 5.4(d,1H); 5.56(d,2H); 5.8(d,1H); 5.9(m,1H); 8.62(d,1H0.

Provenance & Evidence