Ethyl bromoacetate → (6-Methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acid

HRID 593304Notes

Reaction equation

HRID 593304 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[CH2:20][CH2:19][CH2:18]2.Br[CH2:27][C:28]([O:30]CC)=[O:29]>C1COCC1>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[CH:20]([CH2:27][C:28]([OH:30])=[O:29])[CH2:19][CH2:18]2

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 7912DiisopropylamineHCID 141126-Methoxy-alpha-tetraloneHCID 178418339Butyllithium

Product 1

HCID 13574088(6-Methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acidYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyl lithium (3.27 g, 51.04 mmol) was added to a solution of di-isopropyl amine (6.88 g, 68.11 mmol) in THF (50 mL) at −60° C., and the mixture was stirred for 0.5 h. 6-methoxy-1-tetralone (6 g, 34.09 mmol) in THF (10 mL) was slowly added to the reaction mixture, the mixture was stirred for 45 min and ethyl bromoacetate (11.9 g, 71.25 mmol) was added. The reaction mixture was then stirred at room temperature for 16 h and quenched with saturated NH4Cl solution. The reaction mixture was extracted with EtOAc (X2), combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentration to give 5.3 g of the title compound.

Workup

  1. stirringthe mixture was stirred for 45 min
  2. stirringThe reaction mixture was then stirred at room temperature for 16 h
  3. customquenched with saturated NH4Cl solution
  4. extractionThe reaction mixture was extracted with EtOAc (X2)
  5. washwere washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentration

Sources & evidence

ORD record
ord-457fd39f34d84c7ca7fc11c00e481078
Source dataset
uspto-grants-2016_01
Patent number
US09242929B2

Reaction notes

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