C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[C:22][Si](C)(C)C)=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)(C)C.CO.[OH-].[K+]>C(Cl)Cl>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:14]#[C:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]#[CH:5])=[CH:8][CH:9]=2)=[CH:16][CH:17]=1)#[CH:22]Subsequently, the obtained 4,4′-bis(trimethylsilylethynyl)tolan (149 mg, 0.40 mmol) was added with dist. CH2Cl2 (5 mL), dist. MeOH (1 mL) and an aqueous solution of KOH of 50% by mass (0.09 mL). The resultant mixture was then stirred under a nitrogen atmosphere at room temperature for 18 hours to obtain a reaction mixture. After that, the reaction mixture was diluted with CH2Cl2. The organic layer was washed with sat. NaCl, and the washed organic layer was dried with MgSO4. The dried organic layer was filtered and concentrated to obtain a crude product (II). Subsequently, the obtained crude product (II) was separated and purified by silica gel column chromatography (hexane/EtOAc=10/1) to obtain 4,4′-diethynyltolan (60.5 mg, 86% yield (in two steps)).
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