3,4-dihydro-2H-pyran → 2-(1-Adamantyl)-5-bromo-1-(2-tetrahydropyranoxy)benzene

Participants

Reaction Steps

Using the same general procedure as for the preparation of of 4-bromo-2-t-butyl-1-(2-tetrahydropyranoxy) benzene (Compound H), but instead using 12.56 g (40.9 mmol) of 2-(1-adamantyl)-5-bromophenol (Compound G), 1.03 g (4.1 mmol) of pyridinium p-toluenesulfonate, 5.16 g (5.6 ml, 61.3 mmol) of 3,4-dihydro-2H-pyran and 50 ml of dichloromethane produced a clear, orange solution. During aqueous workup, the organic phase was washed with 3×150 ml-portions of sat. aqueous NaHCO3 solution to produce a light yellow solid. Purification by flash chromatography (silica, 3% ethyl acetate in hexane) yielded the title compound as a white solid. PMR (CDCl3):d 1.6-2.1 (21H, m), 3.65-3.72 (1H, m), 3.8-3.93 (1H, m), 5.45 (1H, t, J=2.8 Hz), 7.04-7.08 (2H, m), 7.32 (1H, br s).

Provenance & Evidence