Hydrochloric Acid → HCID 18973020, compound

Participants

Reaction Steps

Pellets of sodium metal (250 mg, 11 mmole) were added to dry ethanol (10 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid 5-isopropoxy-4-azaoxindole (419 mg, 2.22 mmol) was added followed by ethyl-2-thiophene carboxylate (0.59 mL, 688 mg). The mixture was heated at reflux overnight and then cooled to room temperature. After pouring into ice/water, the mixture was acidified using 1N HCl solution and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was subjected to flash chromatography on silica gel eluting successively with chloroform and 49:1 chlorform/methanol. All fractions containing the desired product were combined and concentrated. The residue was again subjected to flash chromatography on silica gel eluting with chloroform. Fractions containing only the desired product were combined and concentrated to give 5-isopropoxy-3-(2-thenoyl)-4-azaoxindole as a yellow gum (300 mg, 45%).

Provenance & Evidence