Pyridine → Ethyl 6-(4-fluorophenyl)-6-oxo-5-phenoxycarbonyloxyhexanoate

HRID 747454Notes

Reaction equation

HRID 747454 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:19])[CH:9]([OH:18])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:26](Cl)(=[O:34])[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:19])[CH:9]([O:18][C:26]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:34])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 18174685Ethyl 6-(4-fluorophenyl)-5-hydroxy-6-oxohexanoate

Product 1

HCID 18174739Ethyl 6-(4-fluorophenyl)-6-oxo-5-phenoxycarbonyloxyhexanoateYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 6-(4-fluorophenyl)-5-hydroxy-6-oxohexanoate (13.5 g), pyridine (4.40 g) and tetrahydrofuran (100 ml) was added dropwise phenyl chlorocarbonate (8.67 g) with stirring under ice-cooling. The mixture was stirred at room temperature for 16 hours. This reaction mixture was concentrated, diluted with ethyl acetate (400 ml) and washed with water (200 ml). The organic layer was dried over anhydrous magnesium sulfate, and concentrated to give ethyl 6-(4-fluorophenyl)-6-oxo-5-phenoxycarbonyloxyhexanoate as a yellow oil (18.1 g, 93%).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 16 hours
  3. concentrationThis reaction mixture was concentrated
  4. additiondiluted with ethyl acetate (400 ml)
  5. washwashed with water (200 ml)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dd4fa991b13d450f9b004234f64b1eba
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Reaction notes

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