Potassium Carbonate → HCID 54563510, compound

HRID 1981991Notes

Reaction equation

HRID 1981991 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:26](=[O:28])[CH3:27])[C:10]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24]Br)=[CH:11][CH:12]=2)[CH:7]=1.[OH:30][C:31]1[C:36]([CH2:37][CH2:38][CH3:39])=[C:35]([OH:40])[CH:34]=[CH:33][C:32]=1[C:41](=[O:43])[CH3:42].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O>[CH3:1][O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:26](=[O:28])[CH3:27])[C:10]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:40][C:35]3[CH:34]=[CH:33][C:32]([C:41](=[O:43])[CH3:42])=[C:31]([OH:30])[C:36]=3[CH2:37][CH2:38][CH3:39])=[CH:11][CH:12]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 53635877HCID 53635877, compound

Product 1

HCID 54563510HCID 54563510, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2 g of [[8-acetyl-7-[2-[2-(2-bromoethoxy)ethoxy]ethoxy]-2-naphthalenyl]oxy]acetic acid methyl ester, 1.0 g of 1-(2,4-dihydroxy-3-propylphenyl)ethanone and 0.9 g of anhydrous potassium carbonate in 40 ml of anhydrous acetone and 14 ml of anhydrous dimethylformamide was stirred at reflux for 16 hours. The solvent was removed in vacuo and residue was dissolved in ethyl acetate, washed with water, dried (magnesium sulfate) and concentrated in vacuo to give an oil which was purified by high pressure liquid chromatography (60% ethyl acetate-hexane) to yield 1.8 g (73%) of [[8-acetyl-7-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]-2-naphthalenyl]oxy]acetic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 16 hours
  2. customThe solvent was removed in vacuo and residue
  3. dissolutionwas dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customto give an oil which
  8. customwas purified by high pressure liquid chromatography (60% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-695255a65fc446fa857227d5a0084411
Source dataset
uspto-grants-1986_06
Patent number
US04594442

Reaction notes

Loading…