2-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonate → 4-[2-(Benzo[b]thiophen-7-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole

Participants

Reaction Steps

In analogy to the procedures described in example 91 a] and b], benzo[b]thiophen-7-ol [J. Chem. Soc., Perkin Trans. 1 (1983), (12), 2973-7] was reacted with methanesulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester [PCT Int. Appl. (2000) WO0008002]) to yield 4-[2-(benzo[b]thiophen-7-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole. Treatment of 4-[2-(benzo[b]thiophen-7-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole with dichloromethyl methyl ether and titanium tetrachloride then gave 7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophene-4-carbaldehyde as a yellow solid. NMR: (CDCl3, 1H, δ, TMS, 300 MHz) 2.45 (s, 3H), 3.12 (t, J=6, 2H), 4.55 (t, J=6, 2H), 6.92 (d, J=8, 1H), 7.39-7.46 (m, 3H), 7.66 (d, J=5, 1H), 7.80 (d, J=8, 1H), 7.95-7.99 (m, 2H), 8.35 (d, J=5, 1H), 10.1 (s, 1H).

Provenance & Evidence