The History of the Birch Reduction

The Birch Reduction was discovered by A.J. Birch in 1940 at the University of Oxford in England. This was during World War 2, and at the time, the Royal Air Force believed that German air pilots were being given cortical hormones to improve their performance.

The RAF wanted to replicate those hormones for their own pilots. The research team began by using female hormones, which are similar to male hormones but have a full aromatic ring as opposed to a partially hydrogenated one. Previous reactions had already demonstrated... Continue Reading...

Scope and Limitations of the Birch Reduction

The birch reduction is used in sterically controlled transformation of aromatic compounds, especially the benzene derivatives. The stereochemical specificity is shown in the figure below. Continue Reading...

Experimental Procedure to Create Product 13

10 ml of anhydrous ammonia (NH3) was condensed at -78 degrees Celsius in a flask connected to an Argon filled balloon. 53 mg of the lithium (Li) metal was dissolved in NH3 with 5 minutes of rapid stirring.

A solution containing 100 mg of methyl enol ether 12 in 2.1 ml of the tetrahydrofuran/2,2,2-trifluoroethanol (THF/CF3CH2OH) was added to the Li/NH3 reagent dropwise over 7 minutes. The reaction mixture was stirred for one hour, and then 500 mg of solid NH4Cl was added portion-wise until the NH3 solution appeared colorless...Continue Reading...