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

HRID 1780609ノート

反応式

HRID 1780609 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-246c55b97d44473789c8e5999f6f96fb
出典データセット
uspto-grants-1997_05
特許番号
US05631208

反応ノート

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