Dimethylformamide → HCID 58963161, compound
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:12][CH3:13])[C:5]2[O:9][CH:8]=[C:7]([CH3:10])[C:6]=2[CH:11]=1.C([Li])(CC)C.CN(C)[CH:21]=[O:22]>C1COCC1>[CH2:12]([C:4]1[C:5]2[O:9][CH:8]=[C:7]([CH3:10])[C:6]=2[CH:11]=[C:2]([CH:21]=[O:22])[CH:3]=1)[CH3:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
5-Bromo-7-ethyl-3-methylbenzofuran 31 (21.25 g, 89 mmoles) was dissolved in dry THF (470 ml) and cooled to −78° C. under a nitrogen atmosphere. Sec-butyl lithium (69.8 ml of a 1.4 M solution, 98 mmoles) was added drop wise to the cooled reaction. The reaction mixture turned a reddish color. Dimethylformamide (51.6 ml, 666 mmoles) was added to the reaction at −78° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was poured into 800 ml of ice/ethyl acetate and the organic layer separated. The aqueous layer was washed with ethyl acetate and the combined organic layer washed with water. The solution was dried over sodium sulfate, filtered, and the solvent removed in vacuo. The crude product was purified by flash chromatography (750 g silica, 8% ethyl acetate in hexanes) to yield 7.02 g of 7-ethyl-3-methylbenzofuran-5-carbaldehyde 32.
Workup
- customwise to the cooled reaction
- temperatureto warm to room temperature
- customthe organic layer separated
- washThe aqueous layer was washed with ethyl acetate
- washthe combined organic layer washed with water
- dry with materialThe solution was dried over sodium sulfate
- filtrationfiltered
- customthe solvent removed in vacuo
- customThe crude product was purified by flash chromatography (750 g silica, 8% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-2b62800637a6488da2c6c49ba76fdfa5
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07273886B2
Reaction notes
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