Tetrahydrofuran → HCID 131723386, 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 3-ethoxy-3-oxopropylzinc bromide (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 (1.1 g, 80%); 1H NMR (300 MHz, CDCl3) δ 0.34 (s, 6 H), 1.29 (d, J=7.2 Hz, 3 H), 1.81 (d, J=7.8 Hz, 2 H), 2.68 (t, J=7.7 Hz, 2 H), 3.02 (t, J=7.7 Hz, 2 H), 4.18 (q, J=7.2 Hz, 2 H), 4.90 (s, 1 H), 4.94 (d, J=7.8 Hz, 1 H), 5.82 (m, 1 H), 7.27 (d, J=7.8 Hz, 2 H), 7.51 (d, J=7.8 Hz, 2 H); 13C NMR (75 MHz, CDCl3) −3.1. 14.5 24.0, 31.2, 36.0, 60.6, 113.7, 128.1, 134.1, 134.9, 136.4, 141.7, 173.0; HRMS (EI) calcd for C16H24O2Si 276.1545, found 276.1548.

Provenance & Evidence