N,N-Dimethylaniline → HCID 9815321, compound

Under argon gas, a solution of diisopropylamine (5.57 g, 55 mmol) in tetrahydrofuran (5 mL) was added dropwise to n-butyllithium (1.53 M in hexane, 31.8 mL, 50 mmol) at 5° C. and the mixture was stirred for 30 minutes. To this was further added a solution of 3-methylpyridine (5.588 g, 30 mmol) in tetrahydrofuran (5 mL) dropwise at 5° C., and the mixture was stirred for 30 minutes. Then, N,N-dimethylaniline (3.64 g, 30 mmol) was added and the mixture was further stirred at 5° C. for 30 minutes. To this was added a solution of glycidol (1.480 g, 20 mmol) in tetrahydrofuran (5 mL) at 5° C., and the reaction was carried out for 2 hours. This reaction mixture was diluted with 30 mL of water for hydrolysis and concentrated under reduced pressure. The residue was extracted with ethyl acetate twice (200 mL each). The organic layers were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residual oil was purified by silica gel column chromatography (Merck's Kieselgel 60, MeOH/ethyl acetate=1/9) to give 2.505 g (isolation yield; 75%) of 4-(3-pyridyl)-1,2-butanediol (yellow oil).

1. stirringthe mixture was stirred for 30 minutes
2. stirringthe mixture was further stirred at 5° C. for 30 minutes
3. waitthe reaction was carried out for 2 hours
4. concentrationconcentrated under reduced pressure
5. extractionThe residue was extracted with ethyl acetate twice (200 mL each)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationAfter filtration
8. distillationthe solvent was distilled off under reduced pressure
9. customthe residual oil was purified by silica gel column chromatography (Merck's Kieselgel 60, MeOH/ethyl acetate=1/9)

ORD record

ord-9c1c44adf5d14094a568f2b9c491d1dc

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06388086B1