Sodium Iodide → 2-{5-Methoxy-2-methyl-4-[5-(4-trifluoromethoxy-phenyl)-pent-4-ynyloxy]-phenoxy}-2-methyl-propionic acid methyl ester

HRID 852430Notes

Reaction equation

HRID 852430 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]([O:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([OH:16])=[CH:10][C:9]=1[CH3:17])([CH3:6])[CH3:5].[F:19][C:20]([F:39])([F:38])[O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]#[C:29][CH2:30][CH2:31][CH2:32]OS(C)(=O)=O)=[CH:24][CH:23]=1.[Na+].[I-].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH3:1][O:2][C:3](=[O:18])[C:4]([O:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH2:32][CH2:31][CH2:30][C:29]#[C:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][C:20]([F:19])([F:38])[F:39])=[CH:23][CH:24]=2)=[CH:10][C:9]=1[CH3:17])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 11616756Methanesulfonic acid 5-(4-trifluoromethoxy-phenyl)-pent-4-ynyl esterHCID 674032312-(4-Hydroxy-5-methoxy-2-methyl-phenoxy)-2-methyl-propionic acid methyl ester

Product 1

HCID 694587952-{5-Methoxy-2-methyl-4-[5-(4-trifluoromethoxy-phenyl)-pent-4-ynyloxy]-phenoxy}-2-methyl-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In analogy to the procedure described in example 1D], 2-(4-hydroxy-5-methoxy-2-methyl-phenoxy)-2-methyl-propionic acid methyl ester was reacted with methanesulfonic acid 5-(4-trifluoromethoxy-phenyl)-pent-4-ynyl ester (example 1G]) in the presence of NaI and Cs2CO3 in acetonitrile under reflux conditions for 4 h, to give 2-{5-methoxy-2-methyl-4-[5-(4-trifluoromethoxy-phenyl)-pent-4-ynyloxy]-phenoxy}-2-methyl-propionic acid methyl ester as colorless oil.

Sources & evidence

ORD record
ord-07d9b98c0c87497bb3f199a90dcbb480
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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