Acetyl chloride → 2-Methyl-8-[(1E)-prop-1-en-1-yl]-4H-chromen-4-one

HRID 1669747ノート

反応式

HRID 1669747 の反応式
[H-].[Na+].[CH2:3]1COC[CH2:4]1.[OH:8][C:9]1[C:14](/[CH:15]=[CH:16]/[CH3:17])=[CH:13][CH:12]=[CH:11][C:10]=1[C:18](=[O:20])[CH3:19].C(Cl)(=O)C>O>[CH3:3][C:4]1[O:8][C:9]2[C:10]([C:18](=[O:20])[CH:19]=1)=[CH:11][CH:12]=[CH:13][C:14]=2/[CH:15]=[CH:16]/[CH3:17]

参加物

6

反応物 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 110084541-{2-Hydroxy-3-[(1E)-prop-1-en-1-yl]phenyl}ethanone

生成物 1

HCID 574388872-Methyl-8-[(1E)-prop-1-en-1-yl]-4H-chromen-4-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

12.52 g (313.2 mmol) of 60% sodium hydride (suspension in mineral oil) are introduced into 300 ml of absolute THF at 10° C. under argon. 18.4 g (104.4 mmol) of 1-{2-hydroxy-3-[(1E)-prop-1-en-1-yl]phenyl}ethanone are slowly added dropwise to the suspension. After 15 min, 9 g (114.9 mmol) of acetyl chloride are added. The reaction mixture is stirred at room temperature overnight. It is hydrolyzed with 300 ml of water and extracted several times with ethyl acetate. Washing of the organic phase with saturated sodium chloride solution is followed by drying over sodium sulfate. The solvent is then removed in vacuo. The residue is taken up in 200 ml of methanol and heated with 50 ml of 20% strength hydrochloric acid at 80° C. for 30 min. The solvent is then removed in vacuo, and the residue is mixed with 400 ml of water. It is extracted several times with dichloromethane. The organic phase is dried over magnesium sulfate and then the solvent is removed in vacuo, and the residue is purified by column chromatography (mobile phase: dichloromethane/methanol 98:2). 10.5 g (50.2% of theory) of the title compound are obtained as a yellow oil.

後処理

  1. extractionextracted several times with ethyl acetate
  2. washWashing of the organic phase with saturated sodium chloride solution
  3. dry with materialby drying over sodium sulfate
  4. customThe solvent is then removed in vacuo
  5. temperatureheated with 50 ml of 20% strength hydrochloric acid at 80° C. for 30 min
  6. customThe solvent is then removed in vacuo
  7. additionthe residue is mixed with 400 ml of water
  8. extractionIt is extracted several times with dichloromethane
  9. dry with materialThe organic phase is dried over magnesium sulfate
  10. customthe solvent is removed in vacuo
  11. customthe residue is purified by column chromatography (mobile phase: dichloromethane/methanol 98:2)

出典と根拠

ORDレコード
ord-4245b3e67c02429c9653ce3161524807
出典データセット
uspto-grants-2011_08
特許番号
US07989633B2

反応ノート

読み込み中…