4-Toluenesulfonyl chloride → pent-4-ynyl tosylate

Participants

Reaction Steps

This compound was synthesized as a colorless oil from pent-4-yn-1-ol (145.0 mg, 132 mmol), TsCl (426.3 mg, 2.24 mmol), Et3N (349.4 mg, 3.44 mmol), and DMAP (210.1 mg, 1.72 mmol) in 74% yield by following general procedure 1.1: 1H NMR (400 MHz, CDCl3, δH) 7.77 (d, J=8.0 Hz, 2H), 7.33 (d, J=8.0 Hz, 2H), 4.24-3.97 (m, 2H), 2.42 (s, 3H), 2.23 (td, J=6.9, 2.6 Hz, 2H), 1.99-1.67 (m, 3H); 13C NMR (100 MHz, CDCl3, δH) 145.06, 133.09, 130.09, 128.12, 82.33, 69.68, 68.98, 27.91, 21.85, 14.90. ESI-MS: 239.1 (M+H+), 261.1 (M+Na4).

Provenance & Evidence