4-Toluenesulfonyl chloride → HCID 13773449, compound

Temperature

25 °C

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);

1. washThis solution was washed with HCl (5w, 100 mL) and brine (100 mL)
2. customdried
3. concentrationconcentrated in Vacuo
4. customto afford the crude product
5. customThis was purified by flash-chromatography on silica gel

ORD record

ord-0d8cdc8ac87f4b4bb788f2d5d6b68e2f

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06534522B2