[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]([C:16]#[C:17][CH3:18])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[C:28]1[CH:33]=[CH:32][C:31](O)=[CH:30][C:29]=1[CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C1COCC1>[F:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[C:28]1[CH:33]=[CH:32][C:31]([O:1][CH2:2][C:3]2[CH:4]=[C:5]([CH:9]([C:16]#[C:17][CH3:18])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=2)=[CH:30][C:29]=1[CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37]Under a nitrogen atmosphere, to a solution of ethyl 3-(3-(hydroxymethyl)phenyl)hex-4-ynoate (100 mg) and 2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-ol (117 mg) in THF (5.8 mL) were added 1,1′-(azodicarbonyl)dipiperidine (164 mg) and tributylphosphine (160 μL) at room temperature, and the mixture was stirred for 16 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (172 mg) as a colorless oil.
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