Sodium hydride → 6-chloro-2-methyl-3(2H)-benzofuranone

HRID 2399781Notes

Reaction equation

HRID 2399781 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5](C(OCC)=O)=[C:4]([O:13][CH:14]([C:16]([O:18]C)=O)[CH3:15])[CH:3]=1.[H-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[C:16](=[O:18])[CH:14]([CH3:15])[O:13][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 19384699Ethyl 4-chloro-2-(1-(methoxycarbonyl)ethoxy)benzoate

Product 1

HCID 193846886-chloro-2-methyl-3(2H)-benzofuranoneYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 4-chloro-2-(1-(methoxycarbonyl)ethoxy)benzoate (7.3 g) and 60% oil dispersion (1.5 g) of sodium hydride in tetrahydrofuran (70 ml) was heated at reflux for 30 minutes, and slowly cooled to room temperature. The reaction mixture was poured into ice-aqueous ammonium chloride and extracted with ether. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to chromatography on silica gel to give 6-chloro-2-methyl-3(2H)-benzofuranone (yield, 1.8 g).

Workup

  1. temperatureat reflux for 30 minutes
  2. additionThe reaction mixture was poured into ice-aqueous ammonium chloride
  3. extractionextracted with ether
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-002630c4d8a744178ec7dd85c9f1a245
Source dataset
uspto-grants-1995_09
Patent number
US05451607

Reaction notes

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