Methyl 4-Formylbenzoate → (4-Methoxycarbonylphenyl)-[3-(methoxymethoxy)pyridin-4-yl]-methanol

Temperature

-70 °C

Next, to a mixture of 3-(methoxymethoxy)pyridine (10.0 g, 71.9 mmol) and diethyl ether (1000 ml), a 1.47 mol/L t-butyllithium n-pentane solution (62 ml, 86.2 mmol) was added dropwise at −70° C. over 25 minutes. After stirring at −70° C. for 1 hour, a solution of 4-methoxycarbonylbenzaldehyde (14.0 g, 90.5 mmol) in diethyl ether (80 mL) was added over 30 minutes and stirred at −70° C. for 1.5 hours. After warming to room temperature, the reaction mixture was poured into saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:80) to give (4-methoxycarbonylphenyl)-[3-(methoxymethoxy)pyridin-4-yl]-methanol (2.06 g, 9.4%) as a yellow powder.

1. stirringstirred at −70° C. for 1.5 hours
2. temperatureAfter warming to room temperature
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with saturated aqueous sodium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:80)

ORD record

ord-eac33b81e0e242efbca7102f7c775833

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439232B2