Sodium hydride → 3-Ethoxy-5-(2-methoxyethoxymethoxyphenyl)-2-cyclohexenone

HRID 1446981ノート

反応式

HRID 1446981 の反応式
[CH2:1]([O:3][C:4]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH2:7][C:6](=[O:17])[CH:5]=1)[CH3:2].[H-].[Na+].[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25]Cl>O1CCCC1>[CH2:1]([O:3][C:4]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[CH2:7][C:6](=[O:17])[CH:5]=1)[CH3:2]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 205521353-Ethoxy-5-(2-hydroxyphenyl)-2-cyclohexenone

生成物 1

HCID 205521113-Ethoxy-5-(2-methoxyethoxymethoxyphenyl)-2-cyclohexenone収率 81.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A suspension of 3-ethoxy-5-(2-hydroxyphenyl)-2-cyclohexenone (32.4 g) in tetrahydrofuran (400 ml) was added slowly to an ice-cooled suspension of sodium hydride (3.34 g) in tetrahydrofuran (75 ml). The mixture was stirred at room temperature for 30 min, cooled in an ice-bath and a solution of methoxyethoxymethyl chloride (20.8 g) in tetrahydrofuran (50 ml) was added dropwise with stirring. The mixture was stirred overnight at room temperature and then was concentrated by the removal of most of the tetrahydrofuran under reduced pressure. The concentrate was diluted with water and extracted with ether. The ethereal extracts were dried and the solvent removed under reduced pressure. The residual oil was purified by column chromatography on silica gel using chloroform for elution to afford the title compound (36.23 g) as a pale yellow oil.

後処理

  1. temperaturecooled
  2. temperaturecooled in an ice-bath
  3. stirringwith stirring
  4. stirringThe mixture was stirred overnight at room temperature
  5. concentrationwas concentrated by the removal of most of the tetrahydrofuran under reduced pressure
  6. additionThe concentrate was diluted with water
  7. extractionextracted with ether
  8. customThe ethereal extracts were dried
  9. customthe solvent removed under reduced pressure
  10. customThe residual oil was purified by column chromatography on silica gel
  11. washfor elution

出典と根拠

ORDレコード
ord-36c00acceb7948dc887009367c8be83b
出典データセット
uspto-grants-1982_02
特許番号
US04315006

反応ノート

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