4-Toluenesulfonyl chloride → HCID 20505538, compound

Participants

Reaction Steps

A solution of t-butyl 3-hydroxypentanoate (5.22 g, 0.3 mol) in dry pyridine (10 ml) was treated with p-toluenesulfonyl chloride (6.3 g, 0.33 mol) dissolved in dry pyridine (15 ml). The resulting solution was stirred at room temperature for 24 h and poured into ice-water (300 ml). The oily layer was separated and dissolved in ether (140 ml). This solution was washed with water (3×150 ml) and dried over anhydrous MgSO4. Evaporation of the ether under reduced pressure gave an oil (7.75 g, 78.7%). ir (neat) νmax : 1725 (C=O of ester) and 1178 cm-1 (sulfonate); 1Hmr (CDCl3) δ: 0.80 (3H, t), 1.38-1.78 (2H, m), 1.42 (9H, s) 2.32-2.62 (2H, m), 2.38 (3H, s), 4.82 (H, m), 7.25 (2H, d) and 7.70 ppm (2H, d). Anal. calcd for C15H24O5S: C 56.94, H 7.65; found: C 58.39, H 7.54.

Provenance & Evidence