Pyridine → HCID 73794978, compound

HRID 1576408Notes

Reaction equation

HRID 1576408 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:3]1[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=CC=CC=1.[Cl:32][CH2:33][C:34](Cl)=[O:35]>O1CCOCC1>[Cl:32][CH2:33][C:34]([O:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:3]1[CH:18]=[CH:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:35]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 68136775HCID 68136775, compound

Product 1

HCID 73794978HCID 73794978, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 6.8 parts of methyl 3-hydroxy5-oxo-2-styrylcyclopent-1-eneheptanoate and 2 parts of pyridine in 80 parts of dioxane is added, at 0°-5°, a solution of 2.4 parts of chloroacetyl chloride in 20 parts of dioxane. The resulting reaction mixture is stirred at that temperature for about 30 minutes, then at room temperature for about 5 hours. At the end of that reaction period the mixture is poured carefully into ice water and the resulting aqueous mixture is extracted with ether. The ether solution is washed successively with dilute hydrochloric acid and dilute aqueous sodium bicarbonate, then dried over anhydrous sodium sulfate and stripped of solvent under reduced pressure. The resulting product is purified by dry column chromatography on silica gel containing 8% of water, using 18% ethyl acetate in benzene, to afford pure methyl 3-chloroacetoxy-5-oxo-2-styrylcyclopent-1-eneheptanoate. This compound is represented by the following structural formula ##SPC7##

Workup

  1. customThe resulting reaction mixture
  2. waitat room temperature for about 5 hours
  3. customAt the end of that reaction period the mixture
  4. extractionthe resulting aqueous mixture is extracted with ether
  5. washThe ether solution is washed successively with dilute hydrochloric acid and dilute aqueous sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe resulting product is purified
  8. dry with materialby dry column chromatography on silica gel containing 8% of water

Sources & evidence

ORD record
ord-c0978ff5712543c39516a676f507875a
Source dataset
uspto-grants-1976_09
Patent number
US03980700

Reaction notes

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