Methyl 4-Formylbenzoate → HCID 22282641, compound

Temperature

-78 °C

4-Bromo-2-methylquinoline, 209a (1.0 g, 4.5 mmol) was dissolved in 10 mL of anhydrous THF and the resulting solution was cooled down to −78° C. A solution of n-BuLi (3.0 mL, 1.6M, 4.8 mmol) was added slowly and the resulting solution was maintained at −78° C. for 5 min. Meanwhile, in another flask methyl 4-formylbenzoate (0.9 g, 5.4 mmol) was dissolved in 20 mL of anhydrous THF and the resulting solution was cooled to −78° C. before the lithium reagent made above was cannulated. The whole mixture was stirred for 30 min before quenched with MeOH. The solution was then diluted with ethyl acetate and washed with H2O and brine. After dried over MgSO4, the organic solution was filtered and concentrated. The residue was purified on silica gel to provide methyl 4-[hydroxy(2-methyl-4-quinolinyl)methyl]benzoate (0.9 g, 65%). MS (AP+): 308 (M+1).

1. temperaturethe resulting solution was maintained at −78° C. for 5 min
2. custombefore quenched with MeOH
3. additionThe solution was then diluted with ethyl acetate
4. washwashed with H2O and brine
5. dry with materialAfter dried over MgSO4
6. filtrationthe organic solution was filtered
7. concentrationconcentrated
8. customThe residue was purified on silica gel

ORD record

ord-85015a11a0ec4eaea0618ee83ac1f73d

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06890915B2