Bis(2-bromoethyl) ether → 4-[[8-Acetyl-7-[2-(2-bromoethoxy)ethoxy]-2-naphthalenyl]oxy]butanoic acid methyl ester

HRID 1981998Notes

Reaction equation

HRID 1981998 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:19](=[O:21])[CH3:20])[C:12]([OH:18])=[CH:13][CH:14]=2)[CH:9]=1.[H-].[Na+].[Br:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30]Br>CN(C)C=O>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:19](=[O:21])[CH3:20])[C:12]([O:18][CH2:30][CH2:29][O:28][CH2:27][CH2:26][Br:25])=[CH:13][CH:14]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydrideHCID 544071994-[(8-Acetyl-7-hydroxy-2-naphthalenyl)oxy]butanoic acid methyl ester

Product 1

HCID 536606914-[[8-Acetyl-7-[2-(2-bromoethoxy)ethoxy]-2-naphthalenyl]oxy]butanoic acid methyl esterYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under an argon atmosphere, 2 g (0.007 mol) of 4-[(8-acetyl-7-hydroxy-2-naphthalenyl)oxy]-butanoic acid methyl ester in 5 ml of anhydrous dimethylformamide was added to a suspension of 0.29 g of sodium hydride in 25 ml of anhydrous dimethylformamide. The mixture was stirred at room temperature for 20 minutes and then 7.7 g of bis-(2-bromoethyl)ether was added and the mixture was stirred at room temperature for 20 hours. The solvent was removed and residual oil was purified by high pressure liquid chromatography using 25% ethyl acetate-hexane to yield 1.6 g (54%) of 4-[[8-acetyl-7-[2-(2-bromoethoxy)ethoxy]-2-naphthalenyl]oxy]butanoic acid methyl ester as an oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hours
  2. customThe solvent was removed
  3. customresidual oil was purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-cf323b28734b449fbb11a68703031ea6
Source dataset
uspto-grants-1986_06
Patent number
US04594442

Reaction notes

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