Potassium Hydroxide → HCID 58081154, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromoindole (8.472 g, 43.216 mmol, toluene-4-sulfonic acid 1,4-dioxa-spiro[4.5]dec-8-yl ester (13.5 g, 43.216 mmol) (prepared according to the procedure described in Journal of the Chemical Society, Perkin Transactions 1 (2002), (20), 2251-2255) and powdered potassium hydroxide (13.239 g, 235.958 mmol) in DMSO (300 ml) was stirred at 80° C. for 6 h. Subsequently, the mixture was poured into ice water. The resulting aqueous mixture was extracted with diethylether (3×), dried (Na2SO4), filtered and the solvent was evaporated in vacuo. The crude residue thus obtained was purified by column chromatography (silica gel; 0-10% DCM/heptane 1:1 as eluent). The desired fractions were collected and evaporated in vacuo to yield D17 (2.897 g, 19.93%) as a white solid.

Provenance & Evidence