Thionyl Chloride → Ethyl 6-(chloromethyl)-2-oxo-2H-1-benzopyran-3-carboxylate

HRID 276973Notes

Reaction equation

HRID 276973 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10](=[O:12])[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][C:7]=2[CH:18]=1.S(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[Cl:21][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10](=[O:12])[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][C:7]=2[CH:18]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10586607HCID 10586607, compound

Product 1

HCID 10659438Ethyl 6-(chloromethyl)-2-oxo-2H-1-benzopyran-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1 g of ethyl 6-hydroxymethyl-2-oxo-2H-1-benzopyran-3-carboxylate (3.9 mmol) and 10 ml of thionyl chloride is refluxed for 3 h. The solution obtained is evaporated under reduced pressure. The residue is re-suspended in 10 ml of dry toluene and the solvent is evaporated off under reduced pressure. The last two steps are repeated twice. The residue obtained is taken up in chloroform and the organic phase is washed three times with 0.1 N HCl solution and then dried over MgSO4. The solvent is removed by distillation under reduced pressure and the residue is recrystallized from CHCl3/Petroleum ether.

Workup

  1. temperatureis refluxed for 3 h
  2. customThe solution obtained
  3. customis evaporated under reduced pressure
  4. customthe solvent is evaporated off under reduced pressure
  5. customThe residue obtained
  6. washthe organic phase is washed three times with 0.1 N HCl solution
  7. dry with materialdried over MgSO4
  8. customThe solvent is removed by distillation under reduced pressure
  9. customthe residue is recrystallized from CHCl3/Petroleum ether

Sources & evidence

ORD record
ord-438769c7c6c2448bbf0cb3ef65cd0d6f
Source dataset
uspto-grants-2002_03
Patent number
US06355658B1

Reaction notes

Loading…