Cesium carbonate → 3-{2-Methyl-4-[5-(4-trifluoromethyl-phenyl)-thiophen-2-ylmethoxy]-phenyl}-propionic acid methyl ester

HRID 1785239

Reaction equation

HRID 1785239 reaction equation
Cl[CH2:2][C:3]1[S:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[CH3:18][O:19][C:20](=[O:31])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=1[CH3:30].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:18][O:19][C:20](=[O:31])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:2][C:3]2[S:4][C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)=[CH:25][C:24]=1[CH3:30]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 13551833Methyl 3-(4-Hydroxy-2-methylphenyl)propanoateHCID 575949792-(Chloromethyl)-5-(4-(trifluoromethyl)phenyl)thiophene

Product 1

HCID 688530103-{2-Methyl-4-[5-(4-trifluoromethyl-phenyl)-thiophen-2-ylmethoxy]-phenyl}-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-Chloromethyl-5-(4-trifluoromethyl-phenyl)-thiophene (0.210 g, 0.760 mmole) and 3-(4-Hydroxy-2-methyl-phenyl)-propionic acid methyl ester (0.147 g, 0.760 mmole) in acetonitrile (5 mL), is added cesium carbonate (0.248 mL, 0.760 mmole) in one portion. The reaction is heated at 50° C. overnight, then concentrated. The residue is loaded to a silica gel column, eluted with ethyl acetate in hexane (0-15%) and concentrated to provide the titled compound as a white solid.

Workup

  1. concentrationconcentrated
  2. washeluted with ethyl acetate in hexane (0-15%)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1a0af10095864711a1b8cd8e75ad68c5
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Linked notes

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