Reaction #1994245

Reaction equation

2-allylpent-4-enoic acid ethyl ester

lithium aluminum hydride

sodium hydroxide

lithium aluminum hydride

→

2-allylpent-4-en-1-ol

Yield 92.8%

Solvents

diethyl ether

water

water

water

Conditions

Workup

1. 1
   OtherThe precipitated white solid was removed from the colorless solution by filtration
2. 2
   OtherSolvent was removed from the solution at reduced pressure

Procedure

To a stirred solution of 2-allylpent-4-enoic acid ethyl ester (prepared above, 14.5 g, 86.2 mmol) in diethyl ether (125 mL) was added lithium aluminum hydride (3.3 g, 87 mmol) in portions slowly over a 30 minute period to cause vigorous gas evolution. When addition of the lithium aluminum hydride was complete, the reaction mixture was stirred for one more hour a room temperature, then 3.5 mL of water were added very slowly. Then 7 mL of a 10 weight percent solution of sodium hydroxide in water were added, followed by the addition of 10 more mL of water. The precipitated white solid was removed from the colorless solution by filtration. Solvent was removed from the solution at reduced pressure to leave 10.1 g of 2-allylpent-4-en-1-ol as a colorless oil whose structure was confirmed by NMR analyses.

Source