Sodium Iodide → Ethyl 4-[5-(5-chloro-2-thienyl)-5-oxo-pentoxy]benzoate

HRID 1197862Notes

Reaction equation

HRID 1197862 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:7](=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11]Cl)=[CH:5][CH:6]=1.[I-].[Na+].OCC[C:19]1[CH:27]=[CH:26][C:22]([C:23]([O-:25])=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-:29].[K+].[K+].[C:34](#N)[CH3:35]>>[Cl:1][C:2]1[S:3][C:4]([C:7](=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11][O:29][C:19]2[CH:20]=[CH:21][C:22]([C:23]([O:25][CH2:34][CH3:35])=[O:24])=[CH:26][CH:27]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 103992482-Chloro-5-(5-chloropentanoyl)thiopheneHCID 222575264-Hydroxyethylbenzoate

Product 1

HCID 490091Ethyl 4-[5-(5-chloro-2-thienyl)-5-oxo-pentoxy]benzoate

Procedure

A mixture consisting of 2-chloro-5-(5-chloropentanoyl)thiophene (3c) (2.13 g, 0.009 mol), sodium iodide (1.1 g, 0.0073 mol), 4-hydroxyethylbenzoate (1.7 g, 0.010 mol), and anhydrous potassium carbonate (6.2 g, 0.045 mol) in acetonitrile (50 ml) was refluxed for 24 hrs., cooled, and filtered. The resulting solution was deprived of the solvent and the residue was taken up with dichloromethane (100 ml). After washing with water and subsequent drying on anydrous sodium sulfate the solution was evaporated to dryness. The resulting solid was crystallized via cyclohexane to pure 5c (2.5 g; 76%). M.p. 87°-89° C. Anal. (C18H19ClO4S).

Workup

  1. temperaturewas refluxed for 24 hrs
  2. temperature, cooled
  3. filtrationfiltered
  4. washAfter washing with water
  5. dry with materialsubsequent drying on anydrous sodium sulfate the solution
  6. customwas evaporated to dryness
  7. customThe resulting solid was crystallized via cyclohexane to pure 5c (2.5 g; 76%)

Sources & evidence

ORD record
ord-d1afb1996cbb41aea5cabeaac064e1bc
Source dataset
uspto-grants-1994_01
Patent number
US05278184

Reaction notes

Loading…