Dimethylformamide → 2(3H)-Benzofuranone, 3,3-dimethyl-

HRID 1453038Notes

Reaction equation

HRID 1453038 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][C:2]1=O.[H-].[Na+].[CH3:13]I.CN([CH:18]=[O:19])C>C1COCC1>[CH3:2][C:3]1([CH3:13])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][C:18]1=[O:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 683822(3H)-Benzofuranone

Product 1

HCID 5956202(3H)-Benzofuranone, 3,3-dimethyl-Yield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3H-Benzofuran-2-one (4.02 g, 30 mmol) dissolved in THF (15 mL) was added cautiously to a suspension of NaH (95% dry, 1.58 g, 66 mmol) in DMF (60 mL) and THF (30 mL) under a nitrogen atmosphere, at 0° C. The mixture was stirred until gas evolution ceased, then MeI (5.6 mL, 90 mmol) was added slowly to avoid boiling over. After MeI addition was complete the reaction further stirred 1 h at room temperature then quenched by carefully pouring onto a mixture of HCl (1N) and ice. The resulting solution was extracted with ether, washed with brine, dried over MgSO4, and chromatographed on silica eluted with a gradient of 5-50% ethyl acetate/hexanes, yielding 3.16 g (65% yield) of the product.

Workup

  1. stirringfurther stirred 1 h at room temperature
  2. customthen quenched
  3. additionby carefully pouring onto a mixture of HCl (1N) and ice
  4. extractionThe resulting solution was extracted with ether
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customchromatographed on silica
  8. washeluted with a gradient of 5-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-95196d6618b24c699cd9df003bb44421
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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