Methanol → 3-(2-Acetylphenyl)-1(R)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)propanol

Participants

Reaction Steps

At 0° C., a 1.5M MeMgBr solution in toluene:THF 1:1 (130 mL, 195 mmol) was added dropwise to a solution of the hydroxyester of Step 3 (11.04 g, 24.1 mmol) (dried in EtOAc and stripped with toluene to remove the H2O) and MeOH (2.0 mL, 49.4 mmol) in 240 mL of anhydrous THF. The reaction mixture was stirred at r.t. for 2.5 h and was then poured into ice cold 25% NH4OAc. The product was extracted into EtOAc, dried over Na2SO4 and purified by flash chromatography on silica with EtOAc:toluene 10:90 and 15:85. [α]D : +23.8° (c=1.04, CHCl3).

Provenance & Evidence