Imidazole → 8-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde

HRID 876383

反応式

HRID 876383 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7]2.N1C=CN=C1.[C:19]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl>[Si:23]([O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7]2)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:25])[CH3:24]

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5993428-Hydroxy-2-quinolinecarboxaldehyde

生成物 1

HCID 585670828-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde収率 95.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 8-hydroxyquinoline-2-carbaldehyde (15.0 g, 86.62 mmol) and imidazole (12.97 g, 190.6 mmol) in anhydrous CH2Cl2 (250 mL) at 0° C. was added tert-butylchlorodimethylsilane (14.36 g, 95.28 mmol). The mixture was allowed to warm slowly to ambient temperature over 16 hours and then partitioned between CH2Cl2 and water. The aqueous phase was extracted with CH2Cl2 and the combined organic phases were washed successively with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel pad filtration eluting with hexanes followed by 19:1 ethyl acetate/hexanes to provide 23.69 g (95%) of desired product as a dark yellow oil.

後処理

  1. custompartitioned between CH2Cl2 and water
  2. extractionThe aqueous phase was extracted with CH2Cl2
  3. washthe combined organic phases were washed successively with saturated NaHCO3, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe residue was purified by silica gel pad filtration
  8. washeluting with hexanes

出典と根拠

ORDレコード
ord-dce37435330049cb8a94a5fc1ae3ea15
出典データセット
uspto-grants-2015_03
特許番号
US08987251B2

関連ノート

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