Potassium Fluoride → HCID 19392525, compound

Participants

Reaction Steps

A solution of 2-chloro-4-ethoxypyrimidine (6.34 g), (1-ethoxyvinyl)-tri-n-butyltin (14.4 g) and bis(triphenylphosphine)palladium(II) chloride (1 g) in DMF (60 ml) was heated at 90° C. for 60 hours. The reaction mixture was cooled to room temperature and potassium fluoride (100 ml of a 10% aqueous solution) was added. The resulting mixture was stirred for 1 hour then filtered through Hyflo supercel filter aid which was rinsed through with ether. The filtrate was extracted with ether (×2) and the combined extracts were washed with brine, then dried, concentrated and chromatographed using ethyl acetate:hexane 1:4 as the eluant to give 1-ethoxy-1-(4-ethoxypyrimidin-2-yl)-ethylene (2.7 g, 35% yield) as an orange oil; IR maximum (film): 1550cm-1 ; 1H NMR (270 MHz): δ1.40(3H,t), 1.50(3H,t), 4.02(2H,q), 4.45(2H,q), 4.58(1H,d), 5.65(1H,d), 6.60(1 H,d), 8.48(1H,d) ppm.

Provenance & Evidence