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

HRID 1690619ノート

反応式

HRID 1690619 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-39af23a067374587906e1d03daa86197
出典データセット
uspto-grants-2012_04
特許番号
US08153647B2

反応ノート

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