Iodoethane → (1,3,5-triethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Suspend sodium hydride (0.23 g, 5.71 mol, 60% dispersion in oil) in tetrahydrofuran (10 mL) and cool to 0° C. Add a solution of (3,5-diethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester (1.0 g, 4.76 mmol) in tetrahydrofuran (10 mL) dropwise. After stirring at 0° C. for 30 min., add iodoethane (0.46 mL, 5.71 mmol). Allow the reaction mixture to warm to room temperature while stirring for 18 hr. Partition between ethyl acetate (100 mL) and saturated aqueous ammonium chloride solution (50 mL). Separate the organic layer, dry (sodium sulfate), filter and concentrate to give (1,3,5-triethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester as an oil (0.92 g, 81%). 1H-NMR (400 MHz, CDCl3) δ 4.09 (q, 2H), 4.01 (q, 2H), 3.33 (s, 2H), 2.58 (m, 4H), 1.38 (t, 3H), 1.20 (m, 9H).

Provenance & Evidence