1-Indanone → HCID 20785939, compound

HRID 252766Notes

Reaction equation

HRID 252766 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]=1

Participants

5

Reactant 3

HCID 67351-IndanoneHCID 12081Methyl 4-bromobenzoateHCID 2724682Lithium diisopropylamide

Product 1

HCID 20785939HCID 20785939, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. temperatureThe reaction was then cooled to −78° C.
  2. temperatureThe solution was slowly warmed to −20° C.
  3. stirringstirred during 4 hours
  4. customThe reaction mixture was quenched with HCL 1M
  5. customthe solvent was evaporated
  6. additionThe residue was diluted in ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude residue was then purified by flash chromatography on silica gel (5-20% AcOEt/HEx)

Sources & evidence

ORD record
ord-74b03379cdb541809d072ed008974606
Source dataset
uspto-grants-2011_01
Patent number
US07868204B2

Reaction notes

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