Potassium Iodide → HCID 14127331, compound

HRID 648699Notes

Reaction equation

HRID 648699 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][CH:3]1[C:13]([O:15][CH3:16])=[O:14].Br[CH2:18][CH2:19][CH2:20][Cl:21].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:21][CH2:20][CH2:19][CH2:18][C:3]1([C:13]([O:15][CH3:16])=[O:14])[C:2](=[O:1])[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 13594461HCID 13594461, compound

Product 1

HCID 14127331HCID 14127331, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5.0 g of methyl 3-oxo-2,3,4,5-tetrahydro-1-benzoxepin-2-carboxylate, 7.1 g of 1-bromo-3-chloropropane, 1.5 g of potassium iodide, 6.3 g of potassium carbonate and 60 ml of acetonitrile is heated under refluxing for 4 hours. After cooling, the inorganic substances are filtered off and the filtrate is concentrated under reduced pressure. The residue is treated with water and then extracted with ethyl acetate. The organic layer is washed with water, dried, and evaporated under reduced pressure. The residue is purified by column chromatography on silica gel (eluant: hexane:ethyl acetate=8:1→2:1), to give 5.5 g of methyl 2-(3-chloropropyl)-3-oxo-2,3,4,5-tetrahydro-1-benzoxepin-2-carboxylate as a colorless oil. Recrystallization from ethanol gives 4.4 g of colorless prisms: m.p. 75°-77° C.

Workup

  1. temperatureis heated
  2. temperatureunder refluxing for 4 hours
  3. temperatureAfter cooling
  4. filtrationthe inorganic substances are filtered off
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. additionThe residue is treated with water
  7. extractionextracted with ethyl acetate
  8. washThe organic layer is washed with water
  9. customdried
  10. customevaporated under reduced pressure
  11. customThe residue is purified by column chromatography on silica gel (eluant: hexane:ethyl acetate=8:1→2:1)

Sources & evidence

ORD record
ord-52f1a086ab2f4622b566249a7fee8229
Source dataset
uspto-grants-1988_04
Patent number
US04736031

Reaction notes

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