Pyridine → Ethyl 6-(5-chloro-2-thienyl)-6-oxo-5-phenoxycarbonyloxyhexanoate

HRID 395654Notes

Reaction equation

HRID 395654 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:18])[CH:8]([OH:17])[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:25](Cl)(=[O:33])[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:18])[CH:8]([O:17][C:25]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:33])[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 18174715Ethyl 6-(5-chloro-2-thienyl)-5-hydroxy-6-oxohexanoate

Product 1

HCID 18174743Ethyl 6-(5-chloro-2-thienyl)-6-oxo-5-phenoxycarbonyloxyhexanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 6-(5-chloro-2-thienyl)-5-hydroxy-6-oxohexanoate (21.6 g), pyridine (6.4 g) and tetrahydrofuran (100 ml) was added dropwise phenyl chlorocarbonate (12.7 g) with stirring under ice-cooling. After the resulting mixture was stirred at room temperature for 16 hours, the 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-(5-chloro-2-thienyl)-6-oxo-5-phenoxycarbonyloxyhexanoate as a yellow oil (30.5 g, quantitative).

Workup

  1. temperaturecooling
  2. stirringAfter the resulting mixture was stirred at room temperature for 16 hours
  3. concentrationthe 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-41ba2461421e4171b5e9e757b36a6f3d
Source dataset
uspto-grants-2003_08
Patent number
US06605629B1

Reaction notes

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