Diisopropylamine → HCID 15546411, compound

Under argon gas, a solution of diisopropylamine (1.67 g, 16.5 mmol) in tetrahydrofuran (5 mL) was added dropwise to n-butyllithium (1.53 M in hexane, 9.8 mL, 15 mmol) at 5° C. and the mixture was stirred for 30 minutes. To this was further added a solution of 3-methylpyridine (2.794 g, 30 mmol) in tetrahydrofuran (5 mL) dropwise at 5° C., and the mixture was stirred for 30 minutes. Then, a solution of phenyl glycidyl ether (1.50 g, 10 mmol) in tetrahydrofuran (5 mL) was added at 5° C. and the reaction was carried out for 2 hours. This reaction mixture was diluted with 20 mL of water for hydrolysis, and extracted with 30 mL of ethyl acetate. The organic layer was washed with 20 mL of water twice and the solvent was distilled off under reduced pressure to give a deep-red oil. This oil was purified by silica gel column chromatography (Merck's Kieselgel 60, hexane/ethyl acetate=1/2) to give 1.911 g (isolation yield: 79%) of 1-O-phenyl-4-(3-pyridyl)-1,2-butanediol (yellow oil).

1. stirringthe mixture was stirred for 30 minutes
2. waitthe reaction was carried out for 2 hours
3. extractionextracted with 30 mL of ethyl acetate
4. washThe organic layer was washed with 20 mL of water twice
5. distillationthe solvent was distilled off under reduced pressure
6. customto give a deep-red oil
7. customThis oil was purified by silica gel column chromatography (Merck's Kieselgel 60, hexane/ethyl acetate=1/2)

ORD record

ord-23421d6fe4054ff592d190936a203e6c

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06388086B1