4-Toluenesulfonyl chloride → HCID 13773449, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of solketal (2.00 mL, 16.0 mmol) in CH2Cl2 (50 mL) was added Et3N (4.50 mL, 32 mmol). A solution of p-toluensulfonyl chloride (4.30 g, 22 mmol) in CH2Cl2 (30 mL) was then added dropwise at 0° C. The resulting solution was stirred at 25° C. for 6 h, then was diluted with CH2Cl2 (50 mL). This solution was washed with HCl (5w, 100 mL) and brine (100 mL), dried and concentrated in Vacuo to afford the crude product. This was purified by flash-chromatography on silica gel using EtOAc/n-hexane as eluant to give the title compound as a colorless oil (2.03 g, 45%): 1H NMR (CDCl3) δ1.31 (s, 3H), 1.34 (s, 3H), 2.45 (s, 3H), 3.77 (q, J=5.1 and 8.7 Hz, 1H), 3.90-4.10 (m, 3H), 4.28 (p, J=5.7 Hz, 1H), 7.35 (d, J=8.1 Hz, 2H), 7.80 (d, J=8.1 Hz, 2H);

Provenance & Evidence