Sodium hydride → HCID 13504772, compound

HRID 1981985Notes

Reaction equation

HRID 1981985 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][CH2:26][O:27][CH2:28][CH2:29][CH2:30]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][CH2:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25][CH2:24][Br:23])=[CH:11][CH:12]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 112307051-Bromo-3-(3-bromopropoxy)propaneHCID 13504771HCID 13504771, compound

Product 1

HCID 13504772HCID 13504772, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere, 1 g of [(8-acetyl-7-hydroxy-2-naphthalenyl)oxy]acetic acid methyl ester was added to a suspension of 0.16 g of 60% sodium hydride in 15 ml of anhydrous dimethylformamide. The mixture was stirred at room temperature for 40 minutes and then 4.75 g of bis(3-bromopropyl)ether was added. The mixture was stirred at room temperature for 20 hours. The mixture was concentrated in vacuo to an oil which was dissolved in ethyl acetate, washed with water and concentrated to give an oil which was purified by column chromatography using 7.5% ethyl acetate-toluene to yield 1 g (60%) of [[8-acetyl-7-[3-(3-bromopropoxy)propoxy]-2-naphthalenyl]oxy]acetic acid methyl ester as an oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 20 hours
  2. concentrationThe mixture was concentrated in vacuo to an oil which
  3. dissolutionwas dissolved in ethyl acetate
  4. washwashed with water
  5. concentrationconcentrated
  6. customto give an oil which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ce378df744d74b5c94f6a7fceb5fbdc1
Source dataset
uspto-grants-1986_06
Patent number
US04594442

Reaction notes

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