Ethyl Bromide → 1-(6-Methylbenzo[d][1,3]dioxol-5-yl)propan-1-ol

HRID 486940ノート

反応式

HRID 486940 の反応式
[CH3:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]2[O:10][CH2:11][O:12][C:4]=2[CH:3]=1.[Mg].Br[CH2:15][CH3:16].[Cl-].[NH4+]>O1CCCC1>[CH3:1][C:2]1[C:7]([CH:8]([OH:9])[CH2:15][CH3:16])=[CH:6][C:5]2[O:10][CH2:11][O:12][C:4]=2[CH:3]=1

参加物

6

反応物 4

HCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 31462426-Methyl-2H-1,3-benzodioxole-5-carbaldehydeHCID 5462224Magnesium

生成物 1

HCID 145148971-(6-Methylbenzo[d][1,3]dioxol-5-yl)propan-1-ol収率 95.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 2.0 g of (6-methyl-1,3-benzodioxol-5-yl)-carboxaldehyde in 15 ml of anhydrous tetrahydrofuran was dropwise added at a room temperature to a Grignard reagent prepared from 0.32 g of magnesium ribbon, 20 ml of anhydrous tetrahydrofuran and 1.4 g of bromoethane, followed by stirring for 2 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture and the obtained mixture was distilled to remove the solvent. The residue was extracted with ethyl acetate and the organic layer was dried over magnesium sulfate and concentrated in a vacuum. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2:8) to obtain 2.27 g of the title compound as a colorless crystal.

後処理

  1. distillationthe obtained mixture was distilled
  2. customto remove the solvent
  3. extractionThe residue was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in a vacuum
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2:8)

出典と根拠

ORDレコード
ord-46bfef24f42d4d77b2c4cad0ace64205
出典データセット
uspto-grants-1994_03
特許番号
US05292901

反応ノート

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