Potassium Hydroxide → HCID 58081154, compound

Participants

Reaction Steps

A mixture of 5-bromoindole (8.472 g, 43.216 mmol), [CAS: 10075-50-0]), toluene-4-sulfonic acid, 1,4-dioxa-spiro[4.5]dec-8-yl ester (13.5 g, 43.216 mmol) [C.A.S. 23551-05-9]; (prepared according to the procedure described in J. Chem. Soc., Perkin Trans. 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 cooled to room temperature and poured into ice water. The resulting aqueous mixture was extracted with Et2O, dried (Na2SO4), and the volatiles were evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; DCM/heptane 1:1 as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D11 (2.897 g, 19.93%) as a white solid.

Provenance & Evidence