Acetonitrile → HCID 67127711, compound

Participants

Reaction Conditions

Reaction Steps

3 g 1-Ethoxy-2,2,6,6-tetramethyl-piperidin-4-one is dissolved in 20 ml dry THF and 0.93 g acetonitrile are added. The mixture is cooled to −78° C. and 9.4 ml n-butyllithium (1.6 M solution in hexane) are added over a period of 30 min. Stirring is continued at −78° C. for 1 h, then the cooling bath is removed. After 2 h stirring at room temperature, the reaction mixture is diluted with MTBE and quenched with ammonium chloride solution. The organic phase is washed with water and brine, dried over sodium sulfate, and the solvent is removed in vacuo. The residue obtained is recrystallized from toluene to obtain the product as colorless crystals. 1H-NMR (CDCl3, 300 MHz): δ 3.78 (q, 2H), 2.43 (s, 2H), 1.93 (s, OH), 1.81 (2 d, 4H), 1.68 (d, 2H), 1.37 (s, 6H), 1.16 (s, 6H), 1.13 (t, 3H). C13-NMR (CDCl3, 75 MHz): δ 117.3, 72.5, 70.0, 58.8, 48.3, 34.8, 33.9, 21.1, 13.2. MS: m/z=241.0 [M+H]+.

Provenance & Evidence