Water → 2-(3-Formyl-4-methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-benzofuran

HRID 1534207ノート

反応式

HRID 1534207 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:27]=[CH:26][C:10]([CH2:11][C:12]2[O:13][C:14]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH3:24])=[C:18]([OH:25])[C:15]=3[C:16]=2[CH3:17])=[CH:9][CH:8]=1.Cl[CH:29]([O:31]C)Cl.O>ClCCl>[CH:29]([C:27]1[CH:26]=[C:10]([CH:9]=[CH:8][C:7]=1[O:6][CH3:5])[CH2:11][C:12]1[O:13][C:14]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH3:24])=[C:18]([OH:25])[C:15]=2[C:16]=1[CH3:17])=[O:31]

参加物

6

反応物 4

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 6451240Aluminum(III) ChlorideHCID 145708892-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propylbenzofuran

生成物 1

HCID 150296522-(3-Formyl-4-methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-benzofuran収率 37%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a suspension of aluminium chloride (214 mg; 1.6 mmole) in dichloromethane (5 mL) cooled at 0° C. was added 2-(p-methoxy-benzyl)-3-methyl-4-hydroxy-5-propyl-benzofuran (100 mg; 0.32 mmoles). A red solution resulted. To this solution was added dropwise dichloromethylmethylether (87 Σl; 0.96 mmole). There was a vigorous reaction and a color change from red to green was observed. Ice and water was then added and the mixture was extracted with ethylacetate. The organic phase was dried (Na2SO4), and concentrated in vacuo and the residue was chromatographed on silica gel. Elution with 10% ethylacetate in hexane yielded 40 mg (37%) of 2-(3-formyl-4-methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-benzofuran.

後処理

  1. customA red solution resulted
  2. customa vigorous reaction
  3. extractionthe mixture was extracted with ethylacetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customthe residue was chromatographed on silica gel
  7. washElution with 10% ethylacetate in hexane

出典と根拠

ORDレコード
ord-85150d2568524fd983ebed0a4d8badfb
出典データセット
uspto-grants-1992_02
特許番号
US05087638

反応ノート

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