Water → 4-Ethyl-2-(1,3-dioxan-4-ylmethoxy)benzaldehyde

HRID 355272

反応式

HRID 355272 の反応式
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:10]=[O:11])=[C:7]([OH:9])[CH:8]=1)[CH3:2].CS(O[CH2:17][CH:18]1[CH2:23][CH2:22][O:21][CH2:20][O:19]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:10]=[O:11])=[C:7]([O:9][CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][O:19]2)[CH:8]=1)[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 102360174-Ethyl-2-hydroxybenzaldehydeHCID 189416164-Methylsulfonyloxymethyl-1,3-dioxane2 回

生成物 1

HCID 189416144-Ethyl-2-(1,3-dioxan-4-ylmethoxy)benzaldehyde収率 55.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A stirred solution of 3.8 grams (0.026 mole) of 5-ethyl-2-formylphenol, 5.0 grams (0.026 mole) of 4-methylsulfonyloxymethyl-1,3-dioxane, and 7.0 grams (0.051 mole) of potassium carbonate in 150 mL of N,N-dimethylformamide was heated at 80° C. for about 18 hours. Analysis by thin layer chromatography (TLC) indicated the reaction was not complete. An additional 2.5 grams (0.013 mole) of 4-methylsulfonyloxymethyl-1,3-dioxane was added, and the reaction mixture was heated at 80° C. for an additional five hours. After this time the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with aqueous 10% lithium chloride, dried with magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel, yielding 3.6 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with aqueous 10% lithium chloride
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residue
  6. customThe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-78ee1c41d0214d01899771ef4a24d8d5
出典データセット
uspto-grants-1998_11
特許番号
USH0001759

関連ノート

読み込み中…