Tetrahydrofuran → HCID 131723387, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5 mol % Pd(Ph3)4 (288 mg, 0.25 mmol) and 1-allyldimethylsilyl-4-iodobenzene (1 Scheme 24, 1.5 g, 5 mmol) in dry THF (10 mL) was added (4-carbethoxyphenyl)zinc iodide (0.5 M solution in THF, 10 mL, 5 mmol). After degassing by bubbling with N2, the reaction mixture was sealed and stirred for 16 h at 60° C. The mixture was treated with saturated NH4Cl (10 mL) and extracted. The organic layer was dried over Na2SO4 and concentrated. The resulting crude product was purified by column chromatography (1:30 ethyl acetate/hexanes) to afford a colorless oil (12 g, 72%); 1H NMR (300 NMz, CDCl3) δ 0.39 (s,6H), 1.46 (t, J=7.5 Hz, 3 H), 1.85 (d, J 8.0 Hz, 2 H), 4.45 (d, J=7.5 Hz, 2 H), 4.94 (s, 1 H), 4.97 (m, 1 H), 5.84 (m, 1 H), 7.65(4 H), 7.70 (d, J=8.0 Hz, 2 H), 8.18 (d, J=8.18 (d, J=8.0 Hz, 2 H); HRMS (EI) calcd for C20H24O2Si 324.1545, found 324.1545.

Provenance & Evidence