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

HRID 1453038

반응식

HRID 1453038 반응식
[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]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2회HCID 24758Sodium hydrideHCID 683822(3H)-Benzofuranone

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-95196d6618b24c699cd9df003bb44421
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473790B2

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