Hydrochloric Acid → HCID 89483049, compound

Temperature

-78 °C

Under nitrogen atmosphere, to a 1000 mL of reaction flask were added dried acetonitrile (15.54 mL, 298.6 mmol) and anhydrous THF (350 mL). The mixture was cooled to −78° C. To the mixture was slowly added n-butyl lithium (171 mL, 1.6 mol/L, 273.7 mmol). The resultant mixture reacted with stirring for 30 min at −78° C. A solution of the compound of Example 4A (65.51 g, 248.8 mmol) in THT (100 mL) was added. The reaction was further kept for 1 hr at −78° C. Then, the reaction was warmed to −20° C. for 30 min, and finally warmed to room temperature for 30 min. The reaction was stopped. Ethyl ether (100 mL) was added to the reaction system to dilute. Water (100 mL) was added for quenching the reaction. pH was adjusted with diluted hydrochloric acid to 3. The organic phase was washed with saturated saline, dried and concentrated. The concentrated organic phase was separated by column chromatography to give 59.5 g of the title compound as pale yellow liquid. Yield: 87.8%. MS (ESI): m/z 273 (M+H)+

1. customUnder nitrogen atmosphere, to a 1000 mL of reaction flask
2. waitThe reaction was further kept for 1 hr at −78° C
3. temperatureThen, the reaction was warmed to −20° C. for 30 min
4. temperaturefinally warmed to room temperature for 30 min
5. additionto dilute
6. customfor quenching
7. customthe reaction
8. washThe organic phase was washed with saturated saline
9. customdried
10. concentrationconcentrated
11. customThe concentrated organic phase was separated by column chromatography

ORD record

ord-b24cdad2fbec42128da14161092d68bd

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249172B2