4-Toluenesulfonyl chloride → HCID 12972966, compound

Participants

Reaction Conditions

Reaction Steps

2,2-Dimethyl-4-tosylmethyl-1,3-dioxolane. 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 (5%, 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) δ 1.31 (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