Water → 1-(tert-Butyldimethylsilyoxymethyl)-4-(2-decynyl)benzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 1; -nonyne (150 mg, 1.2 mmol) in THF (5 mL) at -78° C., was added n-BuLi (0.47 mL, 1.19 mmol). The resulting mixture was stirred for 30 minutes and a solution of [(tertButyldimethylsilyl)oxymethyl]-4-iodomethyl benzene (40) (361 mg, 2 mmol) in THF (1 mL) was added. The reaction mixture was then stirred at -78° C. for 1 hour, allowed to warm to 0° C. and stirred for an additional 30 minutes. At this time, water (2 mL) was slowly added and the mixture was poured into water (50 mL) and Et2O (50 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo to yield a yellow oil. Purification by flash silica gel chromatography (95:05 hexane/EtOAc) afforded (51) (313 mg, 87%) as a colorless oil: Rf 0.85 (95:05 hexane/EtOAc); 1H NMR (CDCl3) δ 7.34 (d, J=8.7 Hz, 2 H), 7.29 (d, J=7.8 Hz, 2 H), 4.75 (s, 2 H), 3.59 (t, J=2.4 Hz, 2 H), 2.24 (tt, J1 =7.2 Hz, J2 =2.4 Hz, 2 H), 1.55 (m, 2 H), 1.42 (m, 2 H), 1.32 (m, 6 H), 0.97 (s, 9 H), 0.92 (t, J=6.9 Hz, 3 H), 0.12 (s, 6 H); 13 C NMR (CDCl3) δ 139.68, 136,38, 127.83, 126.32, 82.74, 77.76, 64.93, 31.91, 29.18, 29.98, 26.08, 24.97, 22.77, 18.97, 14.23, -5.11. ##STR25##

Provenance & Evidence