Diethyl Ether → 6-chloro-2-methyl-3(2H)-benzofuranone

HRID 326293Notes

Reaction equation

HRID 326293 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5](C(OC)=O)=[C:4]([O:12][CH:13]([CH3:18])[C:14]([O:16]C)=O)[CH:3]=1.[H-].[Na+].[Cl-].[NH4+].CCOCC>O1CCCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[C:14](=[O:16])[CH:13]([CH3:18])[O:12][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 867465134-Chloro-2-(2-methoxy-1-methyl-2-oxoethoxy)benzoic acid, methyl ester

Product 1

HCID 193846886-chloro-2-methyl-3(2H)-benzofuranoneYield 44.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the compound of Example 7, Step A, (6.7 g) and sodium hydride (60% in oil, 1.5 g) was heated to reflux in tetrahydrofuran (50 ml). It was then allowed to cool to room temperature over 1.5 hrs. The cooled mixture was treated with aqueous ammonium chloride solution and ether. The ether solution was dried over magnesium sulfate and then evaporated. The oil was subjected to chromatography on silica gel with hexanes/ethyl acetate (25:1) as the eluent. The desired product (1.99 g) was obtained as a low melting solid.

Workup

  1. temperaturewas heated
  2. dry with materialThe ether solution was dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-9635379bfccc45df8e73c298b9ffafad
Source dataset
uspto-grants-1993_12
Patent number
US05268388

Reaction notes

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