Potassium Carbonate → HCID 86630295, compound

Participants

Reaction Steps

A mixture of Ethyl 2-pentynoate (350 mg, 2.77 mmol), 1-iodo-3-(methoxymethoxy)benzene (1.46 g, 5.53 mmol), Phenylboronic acid (675 mg, 5.54 mmol) and K2CO3 (766 mg, 5.54 mmol) in DMF (8 ml)-H2O (2 ml) was stirred at room temperature for 10 min. Then PdCl2(PhCN)2 (10.6 mg, 0.0276 mmol) was added under Ar atmosphere, and the mixture was stirred at room temperature for 24 h. The reaction was quenched with H2O under ice cooling, and the whole was extracted with Et2O. The organic layer was washed with H2O, brine, dried over Na2SO4, then concentrated. Purification by Biotage HPFC (eluent: hexane to hexane/AcOEt, 10:1) gave 2a (25%). 2a: colorless oil; 1H-NMR (CDCl3) δ 1.02 (3H, t, J=7.4 Hz), 1.31 (3H, t, J=7.2 Hz), 2.65 (2H, t, J=7.4 Hz), 3.33 (3H, s), 4.29 (2H, t, J=7.2 Hz), 4.91 (2H, s), 6.65 (1H, m), 6.68 (1H, m), 6.74 (1H, ddd, J=1.0, 2.5, 8.3 Hz), 7.00-7.05 (3H, m), 7.10-7.19 (3H, m).

Provenance & Evidence