Ethyl Acetate → HCID 86668040, compound

Participants

Reaction Steps

2-Bromo-4-methylpyridine (70.0 g, 407 mmol) was added drop wise to a cooled (−78° C.) solution of LDA (2.0 M in toluene/THF/ethyl benzene, 610.4 ml, 1.22 mol) in dry THF (600 ml) for 30 min. ethylchloroformate (132.3 g, 1.22 mol) was added to the resultant reaction mixture with addition funnel at −78° C. and stirring continued for 90 min. Reaction mixture was treated with saturated NH4Cl solution and worked up with ethyl acetate by washing with water, brine followed by drying over anhy. Na2SO4. Organic layer ws concentrated under reduced pressure to obtain crude product which was purified by column chromatography with 10% ethyl acetate in Hexane to furnish title compound as a brown color oily liquid. Yield: 115.0 g (89%). TLC (10% ethyl acetate in hexane) Rf=0.15; LCMS: RtH8=1.475 [M+1]+=315.8 and 317.8; HPLC RtH9=7.30 min (86.7%); 1H NMR (400 MHz, CDCl3) δ 8.38 (d, 1H), 7.56 (t, 1H), 7.34 (dd, 1H), 4.55 (s, 1H), 4.29-4.18 (m, 4H), 1.28 (t, 6H).

Provenance & Evidence