Aluminium lithium hydride → HCID 86662314, compound

Temperature

-20 °C

A solution of ethyl 2-(6-chloropyridin-3-yloxy)-2-methylpropanoate (6.093 g, 25.0 mmol) in dry tetrahydrofuran (80 mL) is cooled to −20° C. (acetonitrile/dry ice bath) under nitrogen atmosphere. A solution of lithium aluminum hydride (1.0 M in THF, 35 ml) was added via drop-wise addition over 10 minutes. The mixture was stirred at −20° C. for 1 hour. The reaction was carefully quenched via addition of water (0.73 ml). The mixture was stirred for 10 minutes and then an aqueous solution of 5% sodium hydroxide (1.34 ml) was added with stirring for 10 minutes. Finally water (1.34 ml) was added and the mixture was stirred for 10 additional minutes. Magnesium sulfate was added and the material was filtered through a plug of celite, rinsing well with tetrahydrofuran. (Note that subsequent stirring of the aluminum salts in dichloromethane (50 ml) and filtering through celite provides additional product). The filtrates were stripped on the rotary evaporator, providing the desired product as a semi-viscous brown oil (4.843 g). (M+H)+=202 m/e.

1. customThe reaction was carefully quenched via addition of water (0.73 ml)
2. stirringThe mixture was stirred for 10 minutes
3. additionan aqueous solution of 5% sodium hydroxide (1.34 ml) was added
4. stirringwith stirring for 10 minutes
5. additionFinally water (1.34 ml) was added
6. stirringthe mixture was stirred for 10 additional minutes
7. additionMagnesium sulfate was added
8. filtrationthe material was filtered through a plug of celite
9. washrinsing well with tetrahydrofuran
10. stirring(Note that subsequent stirring of the aluminum salts in dichloromethane (50 ml)
11. filtrationfiltering through celite
12. customprovides additional product)
13. customThe filtrates were stripped on the rotary evaporator

ORD record

ord-c890f327a0ae4c7cba0c17056b47ba8e

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481540B2