[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][C:14]#[CH:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O1[CH2:21][CH2:20]COO1.C=O.[CH2:24]([NH:26][CH2:27]C)[CH3:25].[OH-].[Na+]>O1CCOCC1.C(O)(=O)C.O>[CH2:24]([N:26]([CH2:20][CH3:21])[CH2:27][C:15]#[C:14][CH2:13][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:25]Heat a mixture of 5-(3,4-dimethoxyphenyl)-pent-1-yne (8 g), water (2.5 cc), trioxan (0.5 g ), 30% formalin (5.5 g), diethylamine (4 g), acetic acid (2.75 g), dioxan (25 cc) and cuprous chloride (0.13 g) at 70° for 15 hours. Make the cooled solution alkaline with 10% aqueous sodium hydroxide and collect the product. Wash the ethereal solution with water and extract with 10% hydrochloric acid (3 × 30 cc). Wash the combined aqueous extracts with ether, make it alkaline with 10% sodium hydroxide solution and extract with ether. Wash and dry the ethereal solution, evaporate the solvent and distil the residue at 0.1 mm Hg to obtain 1-diethylamino-6-(3,4-dimethoxyphenyl)-hex-2-yne.
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