Potassium Carbonate → methyl 2-[(4-{2-[4-(1H-imidazol-1-yl)phenoxy]ethyl}phenoxy)methyl]benzoate

HRID 2111999

Reaction equation

CS([O:5][CH2:6][CH2:7][C:8]1[CH:25]=[CH:24][C:11]([O:12][CH2:13][C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])=[CH:10][CH:9]=1)(=O)=O.[N:26]1([C:31]2[CH:36]=[CH:35][C:34](O)=[CH:33][CH:32]=2)[CH:30]=[CH:29][N:28]=[CH:27]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:26]1([C:31]2[CH:36]=[CH:35][C:34]([O:5][CH2:6][CH2:7][C:8]3[CH:25]=[CH:24][C:11]([O:12][CH2:13][C:14]4[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=4[C:16]([O:18][CH3:19])=[O:17])=[CH:10][CH:9]=3)=[CH:33][CH:32]=2)[CH:30]=[CH:29][N:28]=[CH:27]1

Participants

Conditions

Temperature: 75 °C

Procedure

Methyl 2-[(4-{2-[(methylsulfonyl)oxy]ethyl}phenoxy)methyl]benzoate (0.2 g, 0.55 mmol) and 4-(1H-imidazol-1-yl)phenol (0.11 g, 0.66 mmol) was dissolved in acetonitrile (10 ml) and potassium carbonate (0.09 g, 0.66 mmol) was added. The mixture was stirred over night at 75° C. Remove the acetonitrile by evaporation, dilute with EtOAc (10 ml) and wash the organic phase with Brine three times, dry (MgSO4) and evaporate. This gave 0.268 g of methyl 2-[(4-{2-[4-(1H-imidazol-1-yl)phenoxy]ethyl}phenoxy)methyl]benzoate (yield 90%).

Workup

customRemove the acetonitrile
customby evaporation
additiondilute with EtOAc (10 ml)
washwash the organic phase with Brine three times
dry with materialdry (MgSO4)
customevaporate

Sources & evidence

ORD record: ord-eabb4deeb9264e45adee50c353f77ca3
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521461B2

Linked notes

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