Acetic Acid → 3-(2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(3-{[tert-butyl(diphenyl)silyl]oxy}propyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.44 g, 0.92 mmol) in tetrahydrofuran (4 mL) was treated with tetrabutylammonium fluoride (1.4 mL of a 1 M solution in tetrahydrofuran, 1.4 mmol) and acetic acid (0.16 mL, 2.8 mmol), and stirred at 23° C. for 18 hours. The reaction mixture was diluted with H2O (50 mL) and extracted with dichloromethane (2×50 mL), dried (Na2SO4), and evaporated. Flash chromatography (SiO2, 2.5-100% ethyl acetate/hexanes) provided 3-(2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl)propan-1-ol (0.20 g, 90%) as a colorless oil:

Provenance & Evidence