Sodium methanesulfinate → Ethyl 4-methylsulfonyl-2-oxo-2H-pyran-5-carboxylate

HRID 1085927Notes

Reaction equation

HRID 1085927 reaction equation
[CH3:1][S:2]([O-:4])=[O:3].[Na+].Cl[C:7]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][O:10][C:9](=[O:18])[CH:8]=1>CN(C=O)C.C(Cl)Cl>[CH3:1][S:2]([C:7]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][O:10][C:9](=[O:18])[CH:8]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 14591479ethyl 4-chloro-2-oxo-2H-pyran-5-carboxylate

Product 1

HCID 14591482Ethyl 4-methylsulfonyl-2-oxo-2H-pyran-5-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1.2 g of sodium methylsulfinate are introduced into a solution of 2.02 g of ethyl 4-chloro-2-oxo-2H-pyran-5-carboxylate in DMF, and the mixture is stirred for 2 hours at room temperature. The reaction mixture is diluted with CH2Cl2 and extracted with saturated aqueous NaCl solution. The organic phase is dried with Na2SO4 and evaporated. The distillation residue which has crystallized out is mixed with ether, filtered off with suction and washed with ether. Yield 1.4 g (56.9% of theory); melting point: 95°-97° C.

Workup

  1. extractionextracted with saturated aqueous NaCl solution
  2. dry with materialThe organic phase is dried with Na2SO4
  3. customevaporated
  4. customThe distillation residue which has crystallized out
  5. additionis mixed with ether
  6. filtrationfiltered off with suction
  7. washwashed with ether

Sources & evidence

ORD record
ord-7289936cfdf54f0387ecca2baa3ec1a7
Source dataset
uspto-grants-1991_04
Patent number
US05011944

Reaction notes

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