Potassium Carbonate → 1-{5-[(4-Ethoxybenzyl)oxy]-1-benzofuran-2-yl}ethanone

HRID 1888741

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](=[O:12])[CH3:11])=[CH:7][C:6]=2[CH:13]=1.[CH2:14]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1)[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[CH2:14]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][O:1][C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8]([C:10](=[O:12])[CH3:11])=[CH:7][C:6]=3[CH:13]=2)=[CH:19][CH:18]=1)[CH3:15]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1-(5-hydroxy-1-benzofuran-2-yl)ethanone (2.40 g, 13.7 mmol) in anhydrous DMF (1 mL) were added 4-ethoxybenzyl chloride (2.81 g, 16.5 mmol) and potassium carbonate (3.78 g, 27.4 mmol) and the mixture was stirred at 50° C. overnight. Saturated brine was added thereto, and the mixture was extracted three times with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 1-{5-[(4-ethoxybenzyl)oxy]-1-benzofuran-2-yl}ethanone (6.95 g). This was directly used for the next reaction.

Workup

extractionthe mixture was extracted three times with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-852283389d0e4a479baaeb76ed08dc28
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501804B2

Linked notes

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