4-Toluenesulfonyl chloride → HCID 11076628, compound

Participants

Reaction Steps

2-(2-methoxyethoxy)ethanol 3.06 g (25.6 mmol) and TsCl 6.25 g (32.78 mmol) were dissolved in freshly distilled CH2Cl2, triethylamine (7.1 mL) was added then stirred under argon overnight. Saturated sodium bicarbonate solution (40 mL) and ethyl acetate (100 ml) were added. The organic layer was washed with 1N potassium bisulfate (80 mL), then saturated sodium bicarbonate solution (80 mL), dried over Na2SO4, then dried on rotavap to produce an oil. The product was purified on silica gel flash column with CHCl3:EtOAc=5:1. Product (8) 6.77 g (97% yield) was obtained as a colorless oil. Solvents such as CH3CN and THF may be used instead of CH2Cl2 in the synthesis of compound 8.

Provenance & Evidence