Acetone → [[8-Acetyl-7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)-pentyloxy]-2-naphthalenyl]oxy]acetic acid methyl ester

HRID 2290432Notes

Reaction equation

HRID 2290432 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:23](=[O:25])[CH3:24])[C:10]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br)=[CH:11][CH:12]=2)[CH:7]=1.[OH:27][C:28]1[C:37]([CH2:38][CH2:39][CH3:40])=[C:36]([OH:41])[CH:35]=[CH:34][C:29]=1OC(=O)C.C(=O)([O-])[O-].[K+].[K+].[CH3:48][C:49](C)=[O:50]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:26])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:23](=[O:25])[CH3:24])[C:10]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:41][C:36]3[CH:35]=[CH:34][C:29]([C:49](=[O:50])[CH3:48])=[C:28]([OH:27])[C:37]=3[CH2:38][CH2:39][CH3:40])=[CH:11][CH:12]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium Carbonate2×HCID 202327371-[2,4-Dihydroxy-3-propylphenoxy]ethanoneHCID 54389898HCID 54389898, compound

Product 1

HCID 13505605[[8-Acetyl-7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)-pentyloxy]-2-naphthalenyl]oxy]acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.66 g of [[8-Acetyl-7-(5-bromopentyloxy)-2-naphthalenyl]oxy]acetic acid methyl ester, 0.76 g of 1-[2,4-dihydroxy-3-propylphenoxy]ethanone and 0.81 g of anhydrous potassium carbonate in 30 ml of anhydrous acetone and 10 ml of anhydrous dimethylformamide was stirred at reflux. An additional 0.8 g of anhydrous potassium carbonate was added after 15 hours. Reflux was continued for a total of 22 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to an oil which was treated with ether and water. The organic phase was separated and washed with 1N sodium hydroxide, water and sodium chloride solution. The black oil from concentration of the organic phase was purified by flash column chromatography to yield 1.45 g. mp 87°-89° (69%) of [[8-Acetyl-7 -[5-(4-acetyl-3-hydroxy-2-propylphenoxy)-pentyloxy]-2-napththalenyl]oxy]acetic acid methyl ester.

Workup

  1. temperatureat reflux
  2. temperatureReflux
  3. customwas continued for a total of 22 hours
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo to an oil which
  6. additionwas treated with ether and water
  7. customThe organic phase was separated
  8. washwashed with 1N sodium hydroxide, water and sodium chloride solution
  9. customThe black oil from concentration of the organic phase was purified by flash column chromatography
  10. customto yield 1.45 g

Sources & evidence

ORD record
ord-ec3cbda738574f6ea8c5963b93c0509a
Source dataset
uspto-grants-1986_10
Patent number
US04616091

Reaction notes

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