Isopropyl iodide → 5-Bromo-2,3-dihydro-2-(1-methylethyl)-1H-inden-1-one
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]=[CH:5]2.CN(C)P(N(C)C)(N(C)C)=O.[CH3:23][CH2:24][CH2:25]CCC.C([Li])CCC.C(I)(C)C>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([CH:24]([CH3:25])[CH3:23])[CH2:5]2Participants
7
Conditions
- Temperature
- -78 °C
Procedure
Under nitrogen atmosphere, 100 mg of 5-bromo-1-oxoindene was dissolved in 2 ml of tetrahydrofuran, and cooled down to −78° C. 0.4 ml of hexamethylphosphoramide, 0.3 ml of 1.57 M n-butyllitium hexane solution, and 1.0 ml of isopropyl iodide were added, and the mixture was stirred at −78° C. for 2 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. Ethyl acetate layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure, and the residues were separated and purified by preparative thin-layer chromatography (ethyl acetate/hexane=1/2) to obtain 26 mg of the above compound as a white solid.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washEthyl acetate layer was washed with saturated saline solution
- dry with materialdried with anhydrous sodium sulfate
- distillationThe solvents were distilled outunder reduced pressure
- customthe residues were separated
- custompurified by preparative thin-layer chromatography (ethyl acetate/hexane=1/2)
Sources & evidence
- ORD record
- ord-29960a3fe73d4452940101a44302149c
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902369B2
Reaction notes
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