Water → 2-Methyl-7-(4-dimethylaminophenyl)-1-indanone

Temperature

80 °C

Using a method similar to Example 22, 8.0 g (0.032 mol) of (2), 5.85 g (0.038 mol) of 4-dimethylaminophenylboronic acid and 7.4 g (0.07 mol) of sodium carbonate were placed in 122 ml of dimethoxyethane and 37 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. 142 mg (0.6 mmol) of palladium acetate and 385 mg (1.3 mmol) of tris(o-tolylphenyl)phosphine were added and the reaction mixture was stirred for 4 hours at 80° C. After addition of 150 ml of water, the mixture was extracted 4 times with 100 ml each time of diethyl ether, the ether phase was washed twice with 50 ml each time of water and dried over magnesium sulfate. Removal of the solvent and column filtration through neutral aluminum oxide (dichloromethane) gave 6.5 g of 2-methyl-7-(4-dimethylamino-phenyl)-1-indanone as an oil.

1. custom37 ml of water in the reaction vessel, the mixture was degassed a number of times
2. extractionthe mixture was extracted 4 times with 100 ml each time of diethyl ether
3. washthe ether phase was washed twice with 50 ml each time of water
4. dry with materialdried over magnesium sulfate
5. customRemoval of the solvent and column filtration through neutral aluminum oxide (dichloromethane)

ORD record

ord-d7486efdc3d448e58f608d2a03c0a6aa

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07038070B2