Diisopropylamine → HCID 52951617、化合物

n-BuLi in hexane (1.6 M, 7.6 mL, 11.9 mmol) was added dropwise to a solution of diisopropylamine (1.089 g, 10.9 mmol) in THF (25 mL) at −60 to −70° C. under N2. The mixture was stirred for 10 min. A solution of 5-methoxy-2-methyl-pyridine (1.274 g, 10.35 mmol) in THF (5 mL) was added dropwise to the above mixture. Stirring was continued for another 10 min and 3,4,5-trimethoxybenzonitrile (1.88 g, 9.74 mmol) in THF (5 mL) was added at −70° C. The mixture was stirred at −78° C. for 1 h and then allowed to warm to room temperature. Stirring was continued for another 2 h and the reaction mixture was poured into an ice-cold aqueous NH4Cl solution. The organic layer was separated and the aqueous phase was extracted with ether. The combined organic layers were extracted with a dilute HCl solution. The aqueous layer was washed with ether, neutralized with 10% aqueous NaOH, and extracted with ether. The organic layer was washed with water and dried. The residue was purified by chromatography eluting with CH2Cl2 to give 2-(5-methoxypyridin-2-yl)-1-(3,4,5-trimethoxyphenyl)ethanone (2.31 g, 75.0%).

1. stirringStirring
2. waitwas continued for another 10 min
3. stirringThe mixture was stirred at −78° C. for 1 h
4. stirringStirring
5. waitwas continued for another 2 h
6. customThe organic layer was separated
7. extractionthe aqueous phase was extracted with ether
8. extractionThe combined organic layers were extracted with a dilute HCl solution
9. washThe aqueous layer was washed with ether
10. extractionextracted with ether
11. washThe organic layer was washed with water
12. customdried
13. customThe residue was purified by chromatography
14. washeluting with CH2Cl2

ORDレコード

ord-67840ed8090145518e38cfc7ab623d8b

出典データセット

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07456289B2