Imidazole → 3-(3-Methoxypropoxy)4-[(triisopropylsilyl)oxy]benzaldehyde

HRID 1690619노트

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HRID 1690619 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15].N1C=CN=C1.[CH:21]([Si:24](Cl)([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])([CH3:23])[CH3:22]>CN(C=O)C>[CH3:15][O:14][CH2:13][CH2:12][CH2:11][O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[O:1][Si:24]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:21]([CH3:23])[CH3:22])[CH:6]=[O:7]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 866332964-Hydroxy-3-(3-methoxypropoxy)benzaldehyde

생성물 1

HCID 866333003-(3-Methoxypropoxy)4-[(triisopropylsilyl)oxy]benzaldehyde수율 69%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

In a round bottom flask, 4-hydroxy-3-(3-methoxypropoxy)benzaldehyde (10 g, 47.6 mmol) was introduced. DMF (69 mL) was added. The solution was cooled to 0° C. and imidazole (8.09 g, 118.9 mmol), followed by triisopropylsilyl chloride (10.7 mL, 49.9 mmol) were added. The mixture was stirred for 2 hrs and the solvent was evaporated. A saturated aqueous ammonium chloride was added and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 9/1) to yield 12 g (69%) of the desired product as a yellow oil.

후처리

  1. additionwere added
  2. customthe solvent was evaporated
  3. additionA saturated aqueous ammonium chloride was added
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 9/1)

출처 및 근거

ORD 기록
ord-39af23a067374587906e1d03daa86197
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153647B2

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