1,5-Dibromopentane → HCID 14330013, compound

HRID 2164955Notes

Reaction equation

HRID 2164955 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=1[CH2:19][CH2:20][CH3:21])[CH3:2].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([O:18][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][Br:23])[C:10]=1[CH2:19][CH2:20][CH3:21])[CH3:2]

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium Carbonate2×HCID 14330004Ethyl 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butanoate

Product 1

HCID 14330013HCID 14330013, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3.5 g (0.011 mole) of 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butanoic acid ethyl ester, 15.4 ml (0.11 mole) of 1,5-dibromopentane and 1.2 g (0.0087 mole) of anhydrous potassium carbonate in 60 ml of anhydrous acetone was stirred at reflux for 77 hours. During the reflux period additional 1.4 g portions of potassium carbonate were added at 4,21,28 and 45 hours. The solvent was removed in vacuo and the residue was purified by HPLC using 17% ethyl acetate-hexane to yield 4.35 g (84% yield) of 4-[4-acetyl-3-[(5-bromopentyl)oxy]-2-propylphenoxy]butanoic acid ethyl ester as an oil.

Workup

  1. temperatureat reflux for 77 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-11e79625b5e440b2958dbced3141417d
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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