2,3-Dimethylbenzaldehyde → HCID 44815677, compound

Temperature

-78 °C

To a solution of 1-(diethoxymethyl)-1H-imidazole (698 mg, 4.10 mmol) in anhydrous tetrahydrofuran (7 ml), at −78° C., was added n-butyllithium (2.5 M in hexane, 1.64 ml, 4.1 mmol). The reaction mixture was stirred at −78° C. for 1 h, before addition of a solution of 2,3-dimethylbenzaldehyde (500 mg, 3.73 mmol) in tetrahydrofuran (3 ml). The reaction mixture was stirred at −78° C. for 2 h, warmed to room temperature and quenched with ice cold hydrochloric acid (4M, 20 ml). The reaction mixture was concentrated in vacuo and to the residue was added water (20 ml). The solution was extracted with diethyl ether (2×20 ml) and the aqueous layer was basified by addition of solid sodium hydrogen carbonate. This solution was extracted with ethyl acetate (3×20 ml) and the combined organic phases were dried (MgSO4) and concentrated in vacuo to give the title compound (543 mg)

1. temperaturewarmed to room temperature
2. customquenched with ice cold hydrochloric acid (4M, 20 ml)
3. concentrationThe reaction mixture was concentrated in vacuo and to the residue
4. additionwas added water (20 ml)
5. extractionThe solution was extracted with diethyl ether (2×20 ml)
6. additionthe aqueous layer was basified by addition of solid sodium hydrogen carbonate
7. extractionThis solution was extracted with ethyl acetate (3×20 ml)
8. dry with materialthe combined organic phases were dried (MgSO4)
9. concentrationconcentrated in vacuo

ORD record

ord-7c544e14b83a44cf8609940d8357913c

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07825149B2