Diazomethane → HCID 58894306, compound

HRID 2263943Notes

Reaction equation

HRID 2263943 reaction equation
[Cl:1][C:2]1[C:10]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:15][CH2:16][CH3:17])[CH:3]=1.[N+](=[CH2:20])=[N-]>O1CCCC1.CCOCC>[CH3:20][O:7][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([S:11]([CH3:14])(=[O:12])=[O:13])[C:2]([Cl:1])=[CH:3][C:4]=1[O:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 67071348HCID 67071348, compound

Product 1

HCID 58894306HCID 58894306, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-2-ethoxy-5-methanesulfonylbenzoic acid (2.5 g, 9.0 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 4-chloro-2-ethoxy-5-methanesulfonyl-benzoic acid methyl ester (2.1 g, colorless solids).

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-a81c9f2db9a445bbaa5ed0808e9238e6
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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