2-Phenylethanol → [5-(4-Fluorophenylcarbamoyl)Pyridin-2-Yloxy]Acetic Acid Phenethyl Ester

HRID 1836441Notes

Reaction equation

HRID 1836441 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:21])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:8][N:7]=1.C(O)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(OCC)(=O)C>S(=O)(=O)(O)O.C1(C)C=CC=CC=1>[CH2:1]([O:2][C:3](=[O:22])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:21])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:8][N:7]=1)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 60542-PhenylethanolHCID 8857Ethyl AcetateHCID 10402760[5-(4-Fluorophenylcarbamoyl)Pyridin-2-Yloxy]Acetic Acid Methyl Ester

Product 1

HCID 12146507[5-(4-Fluorophenylcarbamoyl)Pyridin-2-Yloxy]Acetic Acid Phenethyl EsterYield 42%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 1140TolueneSolvent

Procedure

A solution of [5-(4-fluoro-phenylcarbamoyl)-pyridin-2-yloxy]-acetic acid methyl ester (0.020 g, 0.66 mmol), phenethyl alcohol (0.078 mL, 0.66 mmol) and sulfuric acid (1 drop) in toluene (3 mL) was heated at reflux. After 4 h the reaction mixture was poured into ethyl acetate and washed with saturated sodium bicarbonate and dried over sodium sulfate. Removal of the solvents provided a solid. Purification by trituration using ethyl acetate/hexanes gave 0.011 g (42%) of the titled product as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.29 (s 1H); 8.65 (m, 1H); 8.23 (m, 1H); 7.74 (m, 2H); 7.01-7.27 (m, 8H); 4.94 (s, 2H); 4.27 (m, 2H); 2.85 (m, 2H); MS (EI) m/z 393.03 (M−H)−.

Workup

  1. temperatureat reflux
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customRemoval of the solvents
  5. customprovided a solid
  6. customPurification by trituration

Sources & evidence

ORD record
ord-a3645f2838454a99a3460f538a9b612f
Source dataset
uspto-grants-2004_08
Patent number
US06777432B1

Reaction notes

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