Pyridine → Toluene-4-sulfonic acid 2-cyclopropyl-ethyl ester

Participants

Reaction Steps

To a stirred solution of 2-cyclopropylethanol (5.00 g, 58.05 mmol) in dichloromethane (20 mL) was added pyridine (7.03 mL, 86.92 mmol), followed by p-toluenesulfonyl chloride (10.50 g, 55.07 mmol). The reaction mixture was stirred for 16 h, and then partitioned between dichloromethane (100 mL) and water (50 mL). The organic layer was washed with 10% aqueous hydrochloric acid (50 mL), saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford 2-cyclopropylethyl 4-methylbenzenesulfonate as a colorless oil (11.90 g, 96%): 1H NMR (300 MHz, CDCl3) δ 7.80 (d, J=8.3 Hz, 2H), 7.34 (d, J=8.3 Hz, 2H), 4.09 (t, J=6.6 Hz, 2H), 2.45 (s, 3H), 1.57-1.48 (m, 2H), 0.74-0.59 (m, 1H), 0.45-0.36 (m, 2H), 0.08-0.06 (m, 2H).

Provenance & Evidence