CC(P(C(C)(C)C)C1C(C2C=CC=CC=2)=CC=CC=1)(C)C.[C:22]1([CH3:42])[CH:27]=[CH:26][C:25]([C:28]#[C:29][P:30](=[O:41])([O:34][C:35]([CH2:37][CH2:38][CH2:39][Cl:40])=[CH2:36])[O:31][CH2:32][CH3:33])=[CH:24][CH:23]=1>[Au].ClC(Cl)C>[CH2:32]([O:31][P:30]1(=[O:41])[CH:29]=[C:28]([C:25]2[CH:26]=[CH:27][C:22]([CH3:42])=[CH:23][CH:24]=2)[CH:36]=[C:35]([CH2:37][CH2:38][CH2:39][Cl:40])[O:34]1)[CH3:33]Method 1—A gold (Ag(I)) catalyst {[Au(JohnPhos)NCCH3]+SbF6—} [JohnPhos:(2-biphenyl)di-tent-butylphosphine] (11.3 mg, 0.015 mmol) was put into a reaction container, and dichloroethane (0.4 mL) was put thereinto. After stirring at room temperature for 5 minutes, ethyl 5-chloropent-1-en-2-yl p-tolylethynylphosphonate (Example 9, 97.8 mg, 0.3 mmol) diluted with 0.5 mL of dichloroethane was added thereto, and 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 2-ethoxy-4-p-tolyl-6-chloropropyl-1,2-oxaphosphorin 2-oxide (76.3 mg, 78%) which is a title compound.
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