6-Ethoxy-1H-indole

To a stirring solution of 1H-indol-6-ol (0.5 g) in DMF (5.0 mL) at -20 ^C was added NaH (60percent dispersion in oil, 0.18 g). The reaction mixture was warmed to rt and then ethyl bromide (0.81 g) was added and stirring continued for 90 minutes. The reaction mixture was poured into ice water (10 mL) and extracted with ethyl acetate. The organic layer was washed with water, dried over NaTo a stirring solution of 1H-indol-6-ol (0.5 g) in DMF (5.0 mL) at -20 ^C was added NaH (60percent dispersion in oil, 0.18 g). The reaction mixture was warmed to rt and then ethyl bromide (0.81 g) was added and stirring continued for 90 minutes. The reaction mixture was poured into ice water (10 mL) and extracted with ethyl acetate. The organic layer was washed with water, dried over Na (2.34 g, 14.5 mmol) was dissolved in DCM (15 mL) and pyridine (3.52 mL, 43.55 mmol) was added. The solution was cooled to ~ 0 ^C, and a solution of trichloroacetyl chloride (1.28 mL, 11.4 mmol) in DCM (10 mL) was added over the course of about 30 min. The cooling bath was removed and the reaction mixture was stirred at rt overnight. All the volatiles are removed under reduced pressure. The mixture was then stirred with ethanol-water (1:1, 15 mL) for 10 min, and the product was filtered off and dried. Further purification by silica gel flash chromatography eluting with 0-100% ethyl acetate gradient in hexanes to give 2, 2, 2-trichloro-1-(6-ethoxy-1H-indol-3-yl)ethanone (2.41 g).

Molecular Weight:161.20
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:161.084063974
Monoisotopic Mass:161.084063974
Topological Polar Surface Area:25
Heavy Atom Count:12
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes