Water → HCID 14820128, compound

HRID 2166401Notes

Reaction equation

HRID 2166401 reaction equation
[C:1]([C:4]1[C:16]([OH:17])=[CH:15][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]Br)=[C:6]([CH2:18][CH3:19])[CH:5]=1)(=[O:3])[CH3:2].N1C=[CH:23][N:22]=[N:21]1.C(=O)([O-])[O-].[K+].[K+].O.[CH3:32][N:33](C)C=O>>[CH2:18]([C:6]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:22]2[CH:23]=[N:33][CH:32]=[N:21]2)=[CH:15][C:16]([OH:17])=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=1)[CH3:19]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14820101HCID 14820101, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 14820128HCID 14820128, compound

Procedure

A mixture of 0.3 g of 5-(4-acetyl-2-ethyl-5-hydroxyphenoxy)pentylbromide, 0.06 g of triazole, and 0.13 g of potassium carbonate in dimethylformamide was heated at 80°-90° C. for approximately 18 hours. The mixture was poured into acidic water and extracted with ethyl acetate and methylene chloride. The extracts were combined, washed with dilute sodium hydroxide solution, dried over sodium sulfate, and concentrated in vacuo. The residue was twice crystallized from ethyl acetate/hexane to provide the title product having a melting point of 87° C.

Workup

  1. temperaturewas heated at 80°-90° C. for approximately 18 hours
  2. extractionextracted with ethyl acetate and methylene chloride
  3. washwashed with dilute sodium hydroxide solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was twice crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a9209c1702fa4fd4a02d976ac219626b
Source dataset
uspto-grants-1990_07
Patent number
US04945099

Reaction notes

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