Tetrahydrofuran → Ancymidol

Participants

Reaction Steps

To a solution of cyclopropylmagnesium bromide (0.5 M in THF, 9 mL, 4.5 mmol) was added ZnCl2 (612 mg, 4.5 mmol) and LiCl (0.189 mg, 4.5 mmol). To this clear yellow solution was added 18 (1.00 g, 4.5 mmol) in THF and the mixture was stirred for 4 h at rt before being washed with sat. NH4Cl. The organic layer was diluted with EtOAc and washed with sat. NaHCO3 before being dried and evaporated to a brown gum, which was dissolved in toluene and poured over a plug of silica gel (20 g). The plug was washed with hexane-EtOAc (100 mL). The eluants were evaporated to a yellow oil that solidified upon trituration with hexanes. The solid was filtered and dried to afford 374 mg (31%) of 15 as a white solid. Mp=108-110° C.; 1H NMR (300 MHz, CDCl3) δ ppm 9.06 (s, 1H), 8.48 (s, 2H), 7.82 (d, 2H), 7.03 (d, 2H), 3.99 (s, 3H), 1.08 (m, 1H), 0.50-0.31 (m, 4H).

Provenance & Evidence