Methane, dichloromethoxy- → 6-Methoxy-1,3,3-trimethyl-2-oxo-2,3-dihydro-1H-indole-5-carbaldehyde

Participants

Reaction Steps

To a stirred ice-cold solution of 6-Methoxy-1,3,3-trimethyl-1,3-dihydro-indol-2-one (1.0 g, 4.87 mmol) in 30 mL of CH2Cl2 was added TiCl4 (4.80 mL, 43.8 mmol) followed by α,α-dichloromethyl methyl ether (1.98 mL, 21.9 mmol). The reaction was stirred overnight at room temperature and was then quenched with 20 mL of water. The aqueous layer was extracted with CH2Cl2 (2×20 mL) and the combined organic portions were washed successively with satd NaHCO3, brine and water, dried with Na2SO4, and concentrated. The crude product was recrystallized from isopropanol/isopropyl ether to give 680 mg (60%) of a white solid (mp 192–194° C.). A second crop afforded an additional 213 mg for a total yield of 78%.

Provenance & Evidence