Methyl iodide → 2,3-Dihydro-4-hydroxy-7-methoxy-4-methyl-4H-1-benzopyran

HRID 236978ノート

反応式

HRID 236978 の反応式
[CH3:1]I.[Mg].[CH3:4][O:5][C:6]1[CH:16]=[CH:15][C:9]2[C:10](=[O:14])[CH2:11][CH2:12][O:13][C:8]=2[CH:7]=1.[Cl-].[NH4+]>CCOCC>[OH:14][C:10]1([CH3:1])[C:9]2[CH:15]=[CH:16][C:6]([O:5][CH3:4])=[CH:7][C:8]=2[O:13][CH2:12][CH2:11]1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 43875107-methoxy-3,4-dihydro-2H-1-benzopyran-4-oneHCID 5462224Magnesium

生成物 1

HCID 203045882,3-Dihydro-4-hydroxy-7-methoxy-4-methyl-4H-1-benzopyran

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒3 回

実験手順

Methyl iodide (145 g; 64.2 ml) in dry ether (50 ml) was added dropwise with stirring to magnesium turnings (22 g) in dry ether (730 ml). After the initial reaction had ceased the reaction mixture was refluxed for 1/2 hour, cooled and 2,3-dihydro-7-methoxy-4-oxo-4H-1-benzopyran, (77.9 g) in dry ether (440 ml) was added dropwise with stirring. After addition the reaction mixture was refluxed for 1 hour, cooled and the complex was decomposed by the addition of ammonium chloride solution. The ethereal layer was separated, washed with water and dried. Evaporation of the solvent left 76 g of the title compound as an oil (89%). MS and NMR analysis were correct for the required compound.

後処理

  1. customAfter the initial reaction
  2. temperaturewas refluxed for 1/2 hour
  3. temperaturecooled
  4. additionAfter addition the reaction mixture
  5. temperaturewas refluxed for 1 hour
  6. temperaturecooled
  7. customThe ethereal layer was separated
  8. washwashed with water
  9. customdried
  10. customEvaporation of the solvent
  11. waitleft 76 g of the title compound as an oil (89%)

出典と根拠

ORDレコード
ord-372e47da50834c18af7675729686de0d
出典データセット
uspto-grants-1979_06
特許番号
US04159273

反応ノート

読み込み中…