18-Crown-6 → methyl 2-[4-[4-(4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl)-3-fluorophenoxymethyl]phenoxy]propionate
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[N:12]([CH:15]([F:17])[F:16])[C:11]([CH3:18])=[N:10]1.Cl[CH2:20][C:21]1[CH:33]=[CH:32][C:24]([O:25][CH:26]([CH3:31])[C:27]([O:29][CH3:30])=[O:28])=[CH:23][CH:22]=1.O1CCOCCOCCOCCOCCOCC1>CN(C)C=O>[F:16][CH:15]([F:17])[N:12]1[C:13](=[O:14])[N:9]([C:3]2[CH:4]=[CH:5][C:6]([O:8][CH2:20][C:21]3[CH:33]=[CH:32][C:24]([O:25][CH:26]([CH3:31])[C:27]([O:29][CH3:30])=[O:28])=[CH:23][CH:22]=3)=[CH:7][C:2]=2[F:1])[N:10]=[C:11]1[CH3:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
By the method of Example 1, Step I, 0.50 g (0.0019 mole) of 1-(2-fluoro-4-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one (Example 1, Step E) and 0.87 g (0.0038 mole) of methyl 2-(4-chloromethylphenoxy)propionate were reacted in the presence of 0.2 g of 1,4,7,10,13,16-hexaoxacyclooctadecane in 25 mL of N,N-dimethylformamide, yielding 0.80 g of methyl 2-[4-[4-(4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl)-3-fluorophenoxy-methyl]phenoxy]propionate as a colorless oil that solidified upon standing, m.p. 83°-85° C. The NMR and IR spectra were consistent with the proposed structure. NMR: 1.60 (d, 3H, JHH=8.0 Hz); 2.44 (s, 3H); 3.76 (s, 3H); 4.78 (q, 1H, JHH=8.0 Hz); 4.90 (s, 2H); 6.78-7.38 (m, 8H).
Sources & evidence
- ORD record
- ord-3731f01a82cf49948ab1e57ca98c0021
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05798316
Reaction notes
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