Potassium Carbonate → HCID 14330000, compound

HRID 2164969Notes

Reaction equation

HRID 2164969 reaction equation
[Cl:1][C:2]1[C:3]([OH:15])=[C:4]([CH2:12][CH2:13][CH3:14])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH2:16]([O:18][C:19](=[O:45])[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[C:26]([O:33][CH2:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][CH2:40]Br)[C:25]=1[CH2:42][CH2:43][CH3:44])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:16]([O:18][C:19](=[O:45])[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[C:26]([O:33][CH2:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][CH2:40][O:15][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8](=[O:10])[CH3:9])=[C:5]([OH:11])[C:4]=2[CH2:12][CH2:13][CH3:14])[C:25]=1[CH2:42][CH2:43][CH3:44])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 133891721-(5-Chloro-2,4-dihydroxy-3-propylphenyl)ethan-1-oneHCID 14330015HCID 14330015, compound

Product 1

HCID 14330000HCID 14330000, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.850 g of 1-(5-chloro-2,4-dihydroxy-3-propylphenyl)ethanone, 1.811 g of 4-[4-acetyl-3-[3-(3-bromopropoxy)propoxy]-2-propylphenoxy]butanoic acid ethyl ester and 1.0 g of anhydrous potassium carbonate in 65 ml of anhydrous acetone was stirred at reflux for 4 days. Additional 1.0 g portions of potassium carbonate were added after 21 and 30 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to a brown oil. Purification by high pressure liquid chromatography using 20% ethyl acetate-hexane gave 0.516 g (22% yield) of 4-[4-acetyl-3-[3-[3-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)propoxy]propoxy]-2-propylphenoxy]butanoic acid ethyl ester as a yellow oil.

Workup

  1. temperatureat reflux for 4 days
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo to a brown oil
  4. customPurification by high pressure liquid chromatography

Sources & evidence

ORD record
ord-141fca42dcc34c4f8a802a16fb496d36
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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