Sodium hydride → HCID 54141210, compound

HRID 1981993Notes

Reaction equation

HRID 1981993 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:17](=[O:19])[CH3:18])[C:10]([OH:16])=[CH:11][CH:12]=2)[CH:7]=1.[H-].[Na+].[Br:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34]Br>CN(C)C=O>[CH3:1][O:2][C:3](=[O:20])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:17](=[O:19])[CH3:18])[C:10]([O:16][CH2:34][CH2:33][O:32][CH2:31][CH2:30][O:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][Br:23])=[CH:11][CH:12]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 572269Ethane, 1,1'-oxybis[2-(2-bromoethoxy)-HCID 13504771HCID 13504771, compound

Product 1

HCID 54141210HCID 54141210, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere, 2 g of [(8-acetyl-7-hydroxy-2-naphthalenyl)oxy]acetic acid methyl ester was added to a suspension of 0.32 g of 60% sodium hydride in 30 ml of anhydrous dimethylformamide. The mixture was stirred at room temperature for 40 minutes and then 11.6 g of bis[2-[2-bromoethoxy)ethyl]ether was added and the mixture was stirred at room temperature for 20 hours. The resulting dark mixture was concentrated in vacuo to an oil which was dissolved in methylene chloride, washed with water and concentrated to give an oil. Purification by high pressure liquid chromatography (35% ethyl acetate-toluene) gave 3.0 g (80%) of [[8-acetyl-7-[2-[2-[2-(2-bromoethoxy)ethoxy]ethoxy]ethoxy]-2-naphthalenyl]oxy]acetic acid methyl ester as an oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hours
  2. concentrationThe resulting dark mixture was concentrated in vacuo to an oil which
  3. dissolutionwas dissolved in methylene chloride
  4. washwashed with water
  5. concentrationconcentrated
  6. customto give an oil
  7. customPurification by high pressure liquid chromatography (35% ethyl acetate-toluene)

Sources & evidence

ORD record
ord-46d28824778147618a2d83f6ded56aff
Source dataset
uspto-grants-1986_06
Patent number
US04594442

Reaction notes

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