Diazomethane → 5-Chlorosulfonyl-2-ethoxy-4-methoxy-benzoic acid methyl ester

HRID 2263939Notes

Reaction equation

HRID 2263939 reaction equation
[Cl:1][S:2]([C:5]1[C:6]([O:17][CH3:18])=[CH:7][C:8]([O:14][CH2:15][CH3:16])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].[N+](=[CH2:21])=[N-]>O1CCCC1.CCOCC>[CH3:21][O:11][C:10](=[O:12])[C:9]1[CH:13]=[C:5]([S:2]([Cl:1])(=[O:4])=[O:3])[C:6]([O:17][CH3:18])=[CH:7][C:8]=1[O:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 86612878HCID 86612878, compound

Product 1

HCID 866128795-Chlorosulfonyl-2-ethoxy-4-methoxy-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-chlorosulfonyl-2-ethoxy-4-methoxybenzoic acid (13 g, 44 mmol) in tetrahydrofuran was cooled to 5° C. and treated with excess diazomethane in ether solution (prepared from N-methyl-N-nitroso-p-toluenesulfonamide, Aldrich) and stirred for 10 min. Solvent and excess diazomethane was removed by rotary evaporation. The resulting residue was dissolved in dichloromethane and filtered through a plug of silica gel and evaporated. The solids were triturated with ether/hexane to give 13 g of 5-chlorosulfonyl-2-ethoxy-4-methoxy-benzoic acid methyl ester as a colorless solid.

Workup

  1. customSolvent and excess diazomethane was removed by rotary evaporation
  2. dissolutionThe resulting residue was dissolved in dichloromethane
  3. filtrationfiltered through a plug of silica gel
  4. customevaporated
  5. customThe solids were triturated with ether/hexane

Sources & evidence

ORD record
ord-16d1047071434a33bc38acf8d9291a3e
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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