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

HRID 22198Notes

Reaction equation

HRID 22198 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. NMR: 7.6 (d, 1H), 7.1 (m 2H), 4.7 (q, 1H), 1.55 (d, 3H).

Workup

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

Sources & evidence

ORD record
ord-8aec9fe8818e4b988fff34746578e2d3
Source dataset
uspto-grants-1995_06
Patent number
US05428027

Reaction notes

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