Ethyl bromoacetate → 4-Ethoxycarbomethoxy dibenzo[b,d]furan-1-carbaldehyde

HRID 1293442Notes

Reaction equation

O[C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[C:5]([CH:15]=[O:16])=[CH:4][CH:3]=1.[C:17](=O)([O-])[O-:18].[K+].[K+].[CH2:23]([O:25][C:26](=[O:29])CBr)[CH3:24]>CN(C=O)C.O>[CH2:23]([O:25][CH2:26][O:29][C:17]([C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[C:5]([CH:15]=[O:16])=[CH:4][CH:3]=1)=[O:18])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

Intermediate 19 (500 mg, 2.358 mmol) was dissolved in dry DMF (5 ml). Anhydrous potassium carbonate (650 mg, 4.716 mmol) was added to the above solution and was stirred for 10 min. at 80° C. To this was added ethylbromoacetate (2.0 eq.) and the reaction mixture was stirred for 1 h. The reaction mixture was cooled to room temperature and diluted with water (100 ml) and extracted with ethyl acetate (3×50 ml). The organic extract was washed with water (50 ml) and brine solution (25 ml) and dried over anhydrous sodium sulfate. Removal of solvent gave the product as a white solid (550 mg).

Workup

stirringthe reaction mixture was stirred for 1 h
temperatureThe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate (3×50 ml)
extractionThe organic extract
washwas washed with water (50 ml) and brine solution (25 ml)
dry with materialdried over anhydrous sodium sulfate
customRemoval of solvent

Sources & evidence

ORD record: ord-7b6bda4b8c9a4e1db90a5b6dde933d79
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238725B2

Reaction notes

Loading…