Acetone → 4-(2,3-Dihydro-2,2,4,5,6-pentamethylbenzofuran-7-yl)-3-buten-2-one

HRID 1780609노트

반응식

HRID 1780609 반응식
[CH3:1][C:2]1([CH3:16])[CH2:6][C:5]2[C:7]([CH3:15])=[C:8]([CH3:14])[C:9]([CH3:13])=[C:10]([CH:11]=O)[C:4]=2[O:3]1.O.[OH-].[Na+].[CH3:20][C:21]([CH3:23])=[O:22]>>[CH3:1][C:2]1([CH3:16])[CH2:6][C:5]2[C:7]([CH3:15])=[C:8]([CH3:14])[C:9]([CH3:13])=[C:10]([CH:11]=[CH:20][C:21](=[O:22])[CH3:23])[C:4]=2[O:3]1

참가 물질

5

반응물 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 190470682,3-Dihydro-2,2,4,5,6-pentamethylbenzofuran-7-carboxaldehyde

생성물 1

HCID 540298864-(2,3-Dihydro-2,2,4,5,6-pentamethylbenzofuran-7-yl)-3-buten-2-one

실험 절차

To a solution of 19.5 g of the 2,3-dihydro-2,2,4,5,6-pentamethylbenzofuran-7-carboxaldehyde in 65 ml of acetone was added 32 ml of water and 36 g of 1% aqueous solution of sodium hydroxide. After refluxing for 20 hours, the reaction mixture was quenched with 2N hydrochloric acid and the aqueous layer was extracted three times with 50 ml of diethyl ether. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford a crude product. Final purification was carried by recrystallization to afford 17.6 g of 4-(2,3-dihydro-2,2,4,5,6-pentamethylbenzofuran-7-yl)-3-buten-2-one as a yellow plate crystal.

후처리

  1. temperatureAfter refluxing for 20 hours
  2. customthe reaction mixture was quenched with 2N hydrochloric acid
  3. extractionthe aqueous layer was extracted three times with 50 ml of diethyl ether
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford a crude product
  8. customFinal purification
  9. customwas carried by recrystallization

출처 및 근거

ORD 기록
ord-246c55b97d44473789c8e5999f6f96fb
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05631208

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