Water → HCID 22259325, compound

HRID 1610957Notes

Reaction equation

I[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:30]=[CH:29][C:9]([O:10][CH2:11][C:12]2[N:13]=[C:14](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[O:15][CH:16]=2)=[CH:8][CH:7]=1.[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:26][C:25]([F:28])([F:27])[C:22]1[CH:23]=[CH:24][C:19](/[CH:18]=[CH:17]/[C:14]2[O:15][CH:16]=[C:12]([CH2:11][O:10][C:9]3[CH:29]=[CH:30][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:31]4[CH:35]=[CH:34][N:33]=[C:32]4[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:7][CH:8]=3)[N:13]=2)=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of 4-[[4-(4-iodobutyl)phenoxy]methyl]-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (6.00 g), ethyl 3-(1H-imidazol-2-yl)propionate (3.83 g) and potassium carbonate (1.58 g) in DMF (100 ml) was stirred at 70° C. for 23 hr. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was successively washed with water and saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate) and washed with diethyl ether-hexane to give the titled compound (3.69 g) as a colorless amorphous form.

Workup

extractionextracted with ethyl acetate
washThe extract was successively washed with water and saturated brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate)
washwashed with diethyl ether-hexane

Sources & evidence

ORD record: ord-44d5762337b647cb979c8b3af19c072f
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06984653B2

Reaction notes

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