HCID 69706416, compound → HCID 86586629, compound

Participants

Reaction Steps

To a cooled (−100° C.) solution of methyl 4-[4-cyano-2-iodo-phenoxy]-but-2-enoate (4.3 g, 12.5 mmol) (reference example 1 a) in THF: Et2O (4:1, 125 mL) was added dropwise n-buLi (5.5 mL, 2.5 M in hexanes). On complete addition, the reaction mixture was stirred for 15 min then quenched with 1 M aqueous HCl (20 mL). This mixture was diluted with ethyl acetate and washed, sequentially, with water and brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography (eluting with 25% ethyl acetate in hexanes) to give 3.73 g of the title compound. 1H NMR (CDCl3) d 2.63 (dd, 16, 8 Hz, 1H), 2.80 (dd, J=16, 5 Hz, 1H), 3.74 (s, 3H), 3.91 (m, 1H), 4.35 (dd, J=8, 6 Hz, 1H), 4.86 (t, J=8 Hz, 1H), 6.84 (d, J=8 Hz, 1H), 7.47 (m, 2H). MS (EI) m/z 203 (M)+. MS (EI) m/z 217 (M)+.

Provenance & Evidence