CC(P(C(C)(C)C)C1C(C2C=CC=CC=2)=CC=CC=1)(C)C.C(N(CC)CC)C.[C:29]1([CH3:43])[CH:34]=[CH:33][C:32]([C:35]#[C:36][P:37](=[O:42])([OH:41])[O:38][CH2:39][CH3:40])=[CH:31][CH:30]=1.[Cl:44][CH2:45][CH2:46][CH2:47][C:48]#[CH:49]>[Au].ClC(Cl)C>[C:29]1([CH3:43])[CH:30]=[CH:31][C:32]([C:35]#[C:36][P:37](=[O:41])([O:42][C:48]([CH2:47][CH2:46][CH2:45][Cl:44])=[CH2:49])[O:38][CH2:39][CH3:40])=[CH:33][CH:34]=1A gold (Ag(I)) catalyst {[Au(JohnPhos)NCCH3]+SbF6—} [JohnPhos:(2-biphenyl)di-tert-butylphosphine] (11.3 mg, 0.015 mmol) and triethylamine (Et3N) (3.0 mg, 0.03 mmol) were put into a reaction container, and dichloroethane (0.4 mL) was put thereinto. After stirring at room temperature for 5 minutes, ethyl hydrogen p-tolylethynylphosphonate (67.3 mg, 0.3 mmol) diluted with 0.5 mL of dichloroethane was added thereto, and finally, 5-chloropent-1-yne (61.5 mg, 0.6 mmol) was put thereinto. Then, when all of the starting materials disappeared in the TLC, the reaction was allowed to be completed. After the solvent was removed under low atmospheric pressure, the product was separated by chromatography to obtain ethyl 5-chloropent-1-en-2-yl p-tolylethynylphosphonate (68.5 mg, 70%) which is a title compound.
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