Methoxymethyl-triphenylphosphonium chloride → 6-Fluoro-2-(2-methoxyvinyl)-8-(triisopropylsilyloxy)quinoline

Participants

Reaction Conditions

Reaction Steps

(Methoxymethyl)triphenylphosphonium chloride (8.355 g, 24.37 mmol) was dissolved in THF (130 mL), cooled to 0° C., and treated dropwise with a solution of 1M KOtBu in THF (26.5 ml, 26.5 mmol). The mixture was warmed and stirred at ambient temperature for 15 minutes. A solution of 6-fluoro-8-(triisopropylsilyloxy)quinoline-2-carbaldehyde (7.70 g, 22.1 mmol) dissolved in THF (15 mL) was added. The reaction was stirred at ambient temperature for 10 hours. The mixture was concentrated in vacuo and applied directly to a column of SiO2 eluting with a stepped gradient from 1-4% Et2O/hexanes, (4.75 g). 1H NMR (400 MHz, CDCl3) δ 7.86 (d, J=8.6 Hz, 1H), 7.74 (d, J=13 Hz, 1H), 7.23 (d, J=8.6 Hz, 1H), 6.93 (dd, J1=2.8 Hz, J2=8.7 Hz, 1H), 6.88 (dd, J1=2.7 Hz, J2=10.2 Hz, 1H), 6.02 (d, J=12.5 Hz, 1H), 3.77 (s, 3H), 1.47-1.38 (m, 3H), 1.15 (d, 18H).

Provenance & Evidence