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2 (13.4 mg, 0.02 mmol) and dppe (15.9 mg, 0.04 mmol) was added 1-hexyne (0.099 g, 1.2 mmol) via a syringe. Dimethyl acetylenedicarboxylate (0.284 g, 2 mmol) was then added to the solution by a syringe. The reaction mixture was stirred under reflux for 1 h. The progress of the reaction was monitored by GLC. After dimethyl acetylenedicarboxylate was consumed, toluene was evaporated in vacuo. Column chromatography of the residue gave 3a as a colorless oil (n-hexane/AcOEt = 80/20, 0.359 g, yield 98%) and 4a as a colorless oil (n-hexane/AcOEt = 60/40, 0.003 g, yield 2%).
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