1-Cyclopentyl-2-propen-1-ol → 3-(2-Chloro-5-ethoxy-pyridin-4-yl)-1-cyclopentyl-propan-1-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-5-ethoxy-4-iodo-pyridine (1.5 g, 5.3 mmol), 1-cyclopentyl-2-propen-1-ol (0.83 g, 6.61 mmol), sodium acetate (0.54 g, 6.6 mmol), palladium (II) acetate (24 mg, 0.11 mmol) in DMAC (10 mL) was heated to 90° C. under N2 for 16 hours. The reaction mixture was partitioned between 1N HCl and EtOAc. The organic layers were washed with saturated NaHCO3, brine, dried over MgSO4 and concentrated. Purification by silica gel chromatography (0% to 60% EtOAc in hexanes) gave the desired product (1.2 g, 58%). 1H NMR (300 MHz, CDCl3): δ 1.44 (t, J=7.0 Hz, 3H), 1.55-1.87 (m, 8H), 2.75 (m, 2H), 2.86 (m, 3H), 4.11 (q, J=7.0 Hz, 2H), 7.09 (s, 1H), 7.89 (s, 1H).

Provenance & Evidence