Water → HCID 23109600, compound

HRID 968976Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[OH:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=1[O:22][CH3:23].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=1[O:22][CH3:23])(=[O:10])[CH3:9]

Participants

Conditions

Temperature: 100 °C

Procedure

2′-Fluoroacetophenone (1.38 g) and methyl 4-hydroxy-3-methoxybenzoate (1.82 g) were dissolved in dimethylformamide (10 ml), and potassium carbonate (1.45 g) was added. The mixture was stirred at 100° C. for 15 hrs. The reaction mixture was cooled to room temperature, and water was added. The mixture was extracted with ethyl acetate. The organic layer was washed successively with water and brine and dried over sodium sulfate. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the title compound (1.25 g).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionThe mixture was extracted with ethyl acetate
washThe organic layer was washed successively with water and brine
dry with materialdried over sodium sulfate
customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-635fe0eeda104b7782bdb3d21668d43f
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304174B2

Reaction notes

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