Water → cis-1-(tert-Butyldimethylsilyloxymethyl)-4-(2-tridecenyloxymethyl)benzene

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 60 mg of a 60% dispersion of NaH in oil. The dispersion was washed with three 2-mL portions of THF. The NaH was suspended in 5 mL of THF and cooled to 0° C. A solution Of cis-2-tridecen-1-ol (206 mg, 1.1 mmol, 1.1 equiv) in THF (1 mL) was slowly added to the mixture. After 25 minutes the cold bath was removed and stirring was continued for an additional 10 minutes. At this time a solution of (40) (361 mg, 1 mmol) in THF (1 mL) was added and stirring was continued for 12 hours. The mixture was poured into water (20 mL) and ether (25 mL). The organic layer was separated and washed with three 10-mL portions of water. The ether extract was dried (MgSO4) filtered and concentrated by rotary evaporation to yield a yellow oil. Purification by flash silica gel chromatography (95:05 petroleum ether/EtOAc) afforded 341 mg (85%) of the coupled produced (41) as a clear colorless oil: Rf 0.80 (9:1 petroleum ether/EtOAc); 1H NMR (CDCl3) δ 7.20 (s, 4 H), 5.61 (m, 2H), 4.76 (s, 2H), 4.52 (s, 2H), 4.08 (d, J=4.8 Hz, 2H), 2.05 (m, 2H), 1.29 (m, 16 H), 0.97 (s, 9 H), 0.91 (t, J=6.9 Hz, 3 H), 0.12 (s, 6 H); 13C NMR (CDCl3) δ 140.76, 137.04, 127.71, 126.04, 125.98, 71.86, 65.58, 64.80, 31.92, 29.62, 29.56, 29.52, 29.24, 29.36, 27.61, 25.94, 22.69, 18.57, 14.12, -5.25. ##STR8##

Provenance & Evidence