1-Indanone → HCID 20785939, compound
Reaction equation
[Li+].[CH3:2]C([N-]C(C)C)C.[C:9]1(=[O:18])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1.[CH3:19][O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=1>C1COCC1>[O:18]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]1[CH2:2][C:25]1[CH:26]=[CH:27][C:22]([C:21]([O:20][CH3:19])=[O:29])=[CH:23][CH:24]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A 2M LDA solution in THF (4.16 ml, 8.32 mmol) was added to a solution of indanone (1.00 g, 7.57 mmol) in THF (10 ml) at −60° C. The solution was slowly warmed to 0° C. during a period of 15 min. and was agitated for 15 more min. The reaction was then cooled to −78° C. and a solution of methyl-4-bromobenzoate (1.73 g, 7.57 mmol) was slowly added. The solution was slowly warmed to −20° C. and stirred during 4 hours. The reaction mixture was quenched with HCL 1M and the solvent was evaporated. The residue was diluted in ethyl acetate, washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (5-20% AcOEt/HEx) to afford the title compound 271(245 mg, 17%) as a white solid. LRMS: 280.1 (Calc.). 281.1 (found).
Workup
- temperatureThe reaction was then cooled to −78° C.
- temperatureThe solution was slowly warmed to −20° C.
- stirringstirred during 4 hours
- customThe reaction mixture was quenched with HCL 1M
- customthe solvent was evaporated
- additionThe residue was diluted in ethyl acetate
- washwashed with brine
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude residue was then purified by flash chromatography on silica gel (5-20% AcOEt/HEx)
Sources & evidence
- ORD record
- ord-0b8f482924554967847b21795444b4ec
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06897220B2
Reaction notes
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