Triethylamine → HCID 80033541, compound

Participants

Reaction Steps

A solution of 2-thiophenecarbonyl chloride (3.0 g, 23.41 mmol) in anhydrous dioxane (60 mL) was bubbled with argon for 10 minutes. Triethylamine (9.80 mL, 70.22 mmol) was added and the bubbling was maintained for 5 minutes. Bis(triphenylphosphine)palladium(II) dichloride (657 mg, 0.94 mmol), copper iodide (356 mg, 1.87 mmol) and 3,3-diethoxy-1-propyne (3.36 mL, 23.41 mmol) were added, and the reaction mixture was stirred for 2 hours at room temperature, under argon atmosphere. The solution was filtered and water (50 mL) was added to the filtrate. Layers were separated and the aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic layers were washed with a saturated solution of sodium hydrogenocarbonate (50 mL), dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in ethanol (200 mL) and hydrazine hydrate (2.51 g, 35.10 mmol) was added. The reaction mixture was stirred overnight and concentrated in vacuo. The residue was dissolved in ethyl acetate (40 mL) and successively washed with water (40 mL) and brine (40 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide 5-(diethoxymethyl)-3-(thiophen-2-yl)-1H-pyrazole (34a) (4.39 g, 17.40 mmol, 74%) which was used without further purification.

Provenance & Evidence