Carbon Dioxide → HCID 18960410, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.8 g (4.7 mmol) of N-(1,1-dimethylethyl)-1-[2-(tetrahydro-2-pyranyloxy)-ethyl]-1H-indole-3-sulfonamide was dissolved in 30 mL anhydrous THF and cooled to -60° C. under nitrogen atmosphere. To this was added dropwise, with stirring, 8.0 mL (12.8 mmol) 1.6M butyllithium in hexanes and the mixture allowed to warm to 0° C. for 20 minutes then recooled to -60° C. A large excess of crushed dry ice (4 g CO2) was added all at once then the mixture was stirred overnight at ambient temperature. Hydrochloric acid (1N, 15 mL) plus ice was then added and the mixture extracted three times with ethyl acetate. The organic extracts were washed once with brine, dried (Na2SO4) and evaporated in vacuo. The solid residue was triturated and collected by filtration with n-butyl chloride and hexane to afford 1.80 g of the title compound, m.p. 149°-151° C. dec.

Provenance & Evidence