Tetrahydrofuran → HCID 86710477, compound

Participants

Reaction Conditions

Reaction Steps

1.6 M n-butyllithium solution in hexane (14.9 ml; 23.8 mmol; 1.1 eq) is added dropwise to a solution of compound (12) (8 g; 21.7 mmol; 1.0 eq) in 300 ml of anhydrous THF cooled to −78° C. The solution is stirred for 1 hour at −78° C. and then 3-acetylpyridine (2.6 ml; 23.8 mmol; 1.1 eq) is added dropwise. The solution is stirred for 3 hours at −78° C., then for 15 hours at room temperature, and then 100 ml of water and 50 ml of 2 M aqueous sodium hydroxide solution are added. After extraction with ethyl acetate (2×150 ml), the organic phases are combined, dried over MgSO4 and concentrated under reduced pressure. The oil obtained is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate: 4:6) to lead to a mixture of compound (16) and 3-acetylpyridine (6.7 g; 66% by mass of compound (16); 50%) obtained as a yellow oil.

Provenance & Evidence