Tetrabutylammonium Hydroxide → Isohexane ethyl acetate

tetrabutylammonium hydroxide (0.28 g of 40% aqueous solution) was added to a solution of 2,3-dichloro-N-(5,6-dichloro-3-methoxy-2-pyrazinyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide (0.25 g) in 1,2-dimethoxyethane (3.0 mL) at room temperature. After 16 h, the solution was diluted with ethyl acetate (20 mL). The organic solution was washed with aqueous citric acid (10 mL) and brine, dried (MgSO4) and evaporated. Chromatography on silica gel eluting with ethyl acetate/isohexane mixtures gave the title compound containing the SEM group, as a white solid (0.08 g). The solid was dissolved in trifluroacetic acid (2.0 mL) and dichloromethane (2.0 mL) and stirred at room temperature for 1 h. The reaction mixture was concentrated and chromatography on silica gel eluting with ethyl acetate/isohexane mixtures gave the title compound as a white solid (0.027 g).

1. washThe organic solution was washed with aqueous citric acid (10 mL) and brine
2. dry with materialdried (MgSO4)
3. customevaporated

ORD record

ord-2dc3ffcfe7e742dda562567b823bc21d

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662825B2