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

HRID 355272

반응식

HRID 355272 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 102360174-Ethyl-2-hydroxybenzaldehydeHCID 189416164-Methylsulfonyloxymethyl-1,3-dioxane2회

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-78ee1c41d0214d01899771ef4a24d8d5
출처 데이터셋
uspto-grants-1998_11
특허 번호
USH0001759

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