Ethyl bromoacetate → HCID 15512873, compound

HRID 2228658Notes

Reaction equation

HRID 2228658 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].[H-].[Na+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C)C=O.O>[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[C:7]([O:12][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 1199215-Hydroxy-1-tetralone

Product 1

HCID 15512873HCID 15512873, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-dihydro-5-hydroxy-1(2H)-naphthalenone (8.20 g, 50.6 mmol) in N,N-dimethylformamide (80 mL) was added sodium hydride (60% dispersion in liquid paraffin, 2.22 g, 55.6 mmol) at 0° C. and the mixture was stirred at that temperature for 10 minutes. Then, ethyl bromoacetate (9.29 g, 55.6 mmol) was added and the mixture was further stirred at room temperature for 30 minutes. This reaction mixture was poured in water (80 mL) and extracted with 2 portions of ethyl acetate. The organic layers were pooled, washed with water, dried over anhydrous magnesium sulfate (MgSO4), and filtered, and the filtrate was concentrated under reduced pressure. The residue was crystallized from hexane-diisopropyl ether to provide 8.40 g of the title compound. Yield 67%.

Workup

  1. stirringthe mixture was further stirred at room temperature for 30 minutes
  2. extractionextracted with 2 portions of ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was crystallized from hexane-diisopropyl ether

Sources & evidence

ORD record
ord-543d8884c27440f3ae0ff81ebe3357ff
Source dataset
uspto-grants-2002_07
Patent number
US06417213B2

Reaction notes

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