Ethyl bromoacetate → HCID 17761463, compound

HRID 1457323Notes

Reaction equation

HRID 1457323 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]2.C([N-]C(C)C)(C)C.[Li+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[CH:8]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 2668163,4-Dihydro-6,7-dimethoxy-1(2H)-naphthalenoneHCID 2724682Lithium diisopropylamide

Product 1

HCID 17761463HCID 17761463, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,4-Dihydro-6,7-dimethoxy-1(2H)-naphthalenone (10.0 g) was dissolved in tetrahydrofuran (200 ml), and thereto was added dropwise a 2M solution of lithium diisopropylamide in tetrahydrofuran (37 ml) at -70° C. The mixture was stirred for 30 minutes, and thereto was added dropwise ethyl bromoacetate (10.5 g) at -70° C. The mixture was stirred at the same temperature for two hours, and then stirred at 20° C. overnight. The reaction mixture was poured into ice-water, and extracted with diethyl ether. The ether layer was washed successively with water, 10% hydrochloric acid and 10% aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. The resultant was concentrated under reduced pressure to remove the solvent to give ethyl 1,2,3,4-tetrahydro-6,7-dimethoxy-1-oxo-2-naphthaleneacetate (12.0 g) as an oily product.

Workup

  1. stirringThe mixture was stirred at the same temperature for two hours
  2. stirringstirred at 20° C. overnight
  3. extractionextracted with diethyl ether
  4. washThe ether layer was washed successively with water, 10% hydrochloric acid and 10% aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe resultant was concentrated under reduced pressure
  7. customto remove the solvent

Sources & evidence

ORD record
ord-3a9b967250be412487696777fe2882c6
Source dataset
uspto-grants-1998_12
Patent number
US05847159

Reaction notes

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