Acetone → HCID 14329997, compound

HRID 2164964Notes

Reaction equation

HRID 2164964 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:43])[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH2:25][C:26]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]Br)(CCC)[C:27]([C:30](=[O:32])[CH3:31])=[CH:28][CH:29]=1)[CH3:17].C(=O)([O-])[O-].[K+].[K+].[CH3:50][C:51]([CH3:53])=O>CN(C)C=O>[CH2:16]([O:18][C:19](=[O:43])[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:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][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[CH2:50][CH2:51][CH3:53])[CH3:17]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 133891721-(5-Chloro-2,4-dihydroxy-3-propylphenyl)ethan-1-oneHCID 70419125HCID 70419125, compound

Product 1

HCID 14329997HCID 14329997, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.990 g (0.0043 mole) of 1-(5-chloro-2,4-dihydroxy-3-propylphenyl)ethanone, 1.980 g (0.0043 mole) of 4-[4-acetyl-3-[(5-bromopentyl)oxy]-3-propylphenoxy]butanoic acid ethyl ester and 1.2 g (0.0087 mole) of anhydrous potassium carbonate in 40 ml of anhydrous acetone and 20 ml of anhydrous dimethylformamide was stirred at reflux for 22 hours. The reaction mixture was concentrated in vacuo and the residue was purified by HPLC using 25% ethyl acetate-hexane to give 1.008 g (38% yield) of 4-[4-acetyl-3-[5-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)pentyloxy]-2-propylphenoxy]butanoic acid ethyl ester as an oil.

Workup

  1. temperatureat reflux for 22 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-9df86de3caac46fca70e989b601ab1d1
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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