Triethylamine → HCID 66643549, compound

Participants

Reaction Steps

To a solution of tetrahydro-pyran-4-carbaldehyde oxime (6.5 g, 50 mmol) in DMF (47 mL) was added N-chlorosuccinimide (6.95 g, 50 mmol) at room temperature and the after 3 h the mixture was extracted with tert-butylmethylether (100 mL). The organic extract was then added dropwise over 2 h to a solution of ethyl 2-butynoate (61.2 mL, 52.5 mmol) and triethylamine (8.4 mL, 60 mmol) in tert-butylmethylether (47 mL) heated under reflux and the resulting mixture heated overnight. The reaction mixture was then cooled to room temperature and extracted with tert-butylmethylether and washed with aqueous hydrochloric acid solution (1 N). The combined organic phases were dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (4.2 g, 35%) as a light yellow solid. MS: m/e=240.2 [M+H]+.

Provenance & Evidence