Hydrochloric Acid → ethyl(6-bromo-1-oxo-2,3-dihydro-1H-inden-2-yl)acetate

HRID 273218

Reaction equation

HRID 273218 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Br:13][C:14]1[CH:22]=[C:21]2[C:17]([CH2:18][CH2:19][C:20]2=[O:23])=[CH:16][CH:15]=1.Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][CH:19]1[CH2:18][C:17]2[C:21](=[CH:22][C:14]([Br:13])=[CH:15][CH:16]=2)[C:20]1=[O:23])[CH3:30]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 7912DiisopropylamineHCID 11430Potassium CarbonateHCID 1397781-Indanone, 6-bromo-HCID 178418339Butyllithium

Product 1

HCID 86592225ethyl(6-bromo-1-oxo-2,3-dihydro-1H-inden-2-yl)acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

n-Butyllithium (14 mL, 2 M in pentane) was added dropwise to a solution of diisopropylamine (2.86 g, 28 mmol) in tetrahydrofuran (60 mL) cooled to −70° C. After 30 minutes of stirring at −70° C., the mixture was treated with 6-bromo-1-indanone (4.8 g, 22.7 mmol), prepared according to the procedure described in J. Org. Chem., 49:4226-423 (1984), in two portions over 5 minutes. After 10 minutes, the mixture was allowed to warm to −50° C. and was treated with ethyl bromoacetate (4.8 g, 28 mmol). The mixture was allowed to warm to −10° C. and was stirred at −10 to −15° C. for 1 hour. The reaction was quenched by careful addition of water (60 mL) followed by isopropyl acetate (60 mL). The organic layer was separated, washed with aqueous HCl (50 mL, prepared by adjusting the pH of water to 2 with conc. HCl), and then aqueous potassium carbonate (50 mL, 5%). The organic layer was concentrated under vacuum to provide the title compound which was used in the next step without further purification.

Workup

  1. customprepared
  2. wait, 49:4226-423 (1984), in two portions over 5 minutes
  3. waitAfter 10 minutes
  4. temperatureto warm to −50° C.
  5. temperatureto warm to −10° C.
  6. stirringwas stirred at −10 to −15° C. for 1 hour
  7. customThe reaction was quenched by careful addition of water (60 mL)
  8. customThe organic layer was separated
  9. washwashed with aqueous HCl (50 mL
  10. customprepared
  11. concentrationThe organic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-581b20ae97d649d295c78b1ed3c6fe09
Source dataset
uspto-grants-2008_11
Patent number
US07456196B2

Linked notes

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