Aluminium lithium hydride → HCID 12277043, compound

Temperature

0 °C

A solution of methyl (4E)-4-methyl-5-phenyl-4-pentenoate (3.5 g, 0.016 mol) in dry THF (100 ml) was treated, at −78° C. under nitrogen, with solid lithium aluminum hydride (1 g, 0.025 mol) in one portion. After 5 minutes, the cooling bath was removed and the reaction allowed reaching room temperature and then cooled to 0° C. and treated successively with water (1 ml), 5% aqueous sodium hydroxide (3 ml) and water (1 ml). The reaction was stirred at room temperature for 30 minutes. Anhydrous solid sodium sulfate was added (3 g) and stirring continued for 5 minutes. The solid was filtered off, rinsed with diethyl ether and the filtrate was evaporated under vacuum. The product was purified by bulb-to-bulb distillation (84° C./0.002 mbar). 2.88 g (yield=100%) of the desired product were obtained.

1. customthe cooling bath was removed
2. customallowed reaching room temperature
3. additiontreated successively with water (1 ml), 5% aqueous sodium hydroxide (3 ml) and water (1 ml)
4. additionAnhydrous solid sodium sulfate was added (3 g)
5. stirringstirring
6. waitcontinued for 5 minutes
7. filtrationThe solid was filtered off
8. washrinsed with diethyl ether
9. customthe filtrate was evaporated under vacuum
10. distillationThe product was purified by bulb-to-bulb distillation (84° C./0.002 mbar)

ORD record

ord-da87a77f9e2d4c939576883b130145ba

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815792B2