4-Toluenesulfonyl chloride → HCID 86695317, compound

Participants

Reaction Conditions

Reaction Steps

A 10 mL round bottom flask was charged with 21 (0.48 g, 2.12 mmol), Et3N (590 μL, 4.24 mmol), 4-dimethylaminopyridine (0.03 g, 0.21 mmol), and CH2Cl2 (5 mL) under an argon atmosphere. The solution was cooled to 0° C., and a solution of 4-toluenesulfonyl chloride (0.61 g, 3.18 mmol) in CH2Cl2 (1 mL) was added drop wise. The mixture was stirred vigourously for 4 hours at room temperature. The reaction mixture was treated with saturated aqueous NaHCO3 (10 mL). After stirring at room temperature for 20 minutes, ethyl acetate (20 mL) was added. The organic layer was separated and washed with water (3×100 mL) and brine (50 mL), and dried over MgSO4. The solution was filtered and the solvent was removed in vacuo. Flash chromatography of the residue (SiO2, using a gradient of 2:1 hexanes/CH2Cl2 to 1:1 hexanes/CH2Cl2) provided 22 (0.68 g, 84% yield, 84% Z as determined by 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 7.79 (2H, d, J=8.3 Hz), 7.33 (2H, d, J=8.9 Hz), 5.19-5.40 (2H, m), 4.02 2H, t, J=6.4 Hz), 2.44 (3H, s), 1.91-2.08 (4H, m), 1.66-1.71 (2H, m), 1.25 (16H, m), 0.88 (3H, t, J=7.0 Hz); 13C NMR (100 Hz, CDCl3): δ 144.8, 144.7, 133.3, 131.8, 129.9, 128.0, 127.8, 127.4, 70.2, 32.6, 32.0, 29.7 (2C), 29.6 (2C), 29.5, 29.4, 29.0, 27.3, 23.1, 22.8, 14.3; HRMS (FAB): 381.2477, [C22H36O3S+H]+ requires 381.2458.

Provenance & Evidence