2,5-Dimethoxyaniline → [16-(t-Butyldimethylsilanyloxy)hexadecyl]-(2,5-dimethoxyphenyl)amine

2,5-Dimethoxyaniline (352.3 mg) was dissolved in 20 ml of tetrahydrofuran, and then 2.3 ml of n-butyl lithium (1.0 M solution in hexane), 3 ml of a solution of (16-bromohexadecyloxy)-t-butyldimethylsilane in tetrahydrofuran, and 0.20 ml of 1,4-dioxane were added to this solution at 0° C. The reaction mixture was refluxed for 24 hours while stirring. Saturated ammonium chloride solution was added to the reaction mixture, which was then extracted three times with dichloromethane. The organic layer was washed with saline solution and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel chromatography (heptane:ethyl acetate=7:3) gave [16-(t-butyldimethylsilanyloxy)hexadecyl]-(2,5-dimethoxyphenyl)amine as a yellow oil at a 50% yield.

1. temperatureThe reaction mixture was refluxed for 24 hours
2. extractionwas then extracted three times with dichloromethane
3. washThe organic layer was washed with saline solution
4. dry with materialdried over magnesium sulfate
5. distillationthe solvent was distilled off under reduced pressure
6. customPurification of the residue by silica gel chromatography (heptane:ethyl acetate=7:3)

ORD record

ord-92666152c73f4e68b19c89e26e7c9a04

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07893304B2