Isopropanol → 1-Quinolin-6-ylcyclopropanecarbaldehyde

HRID 1099058ノート

反応式

HRID 1099058 の反応式
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]1[CH2:15][O:14][CH2:13][CH2:12]1.[N:16]1[C:25]2[C:20](=[CH:21][C:22](C3(C#N)CC3)=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.C(O)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:16]1[C:25]2[C:20](=[CH:21][C:22]([C:11]3([CH:15]=[O:14])[CH2:13][CH2:12]3)=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

参加物

7

反応物 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 21225700DiisobutylaluminumhydrideHCID 668128401-(Quinolin-6-yl)cyclopropanecarbonitrile

生成物 1

HCID 592162771-Quinolin-6-ylcyclopropanecarbaldehyde収率 95.2%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-2.5 °C

実験手順

Diisobutylaluminum hydride in THF (1.0 M, 96 mL, 0.096 mol) was added to a solution of 1-quinolin-6-ylcyclopropanecarbonitrile (12.4 g, 0.0639 mol) in toluene (120 mL) at −78° C. under an atmosphere of nitrogen. The reaction mixture was allowed to warm to −5 to 0° C., and stirred at that temperature for 3 h. The mixture was re-cooled to −60° C. Isopropyl alcohol (10 mL) was carefully added dropwise. After stirring for 30 min, the mixture was warmed to −5 to 0° C. The mixture was diluted with ethyl acetate, quenched with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4, filtered through a pad of silica gel and washed with ethyl acetate in hexanes (40%). The filtrate was concentrated to yield the desired 1-quinolin-6-ylcyclopropanecarbaldehyde (12 g, 95.1%).

後処理

  1. temperatureThe mixture was re-cooled to −60° C
  2. stirringAfter stirring for 30 min
  3. temperaturethe mixture was warmed to −5 to 0° C
  4. customquenched with water
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered through a pad of silica gel
  9. washwashed with ethyl acetate in hexanes (40%)
  10. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-379cabd915184830829d81aa5a265720
出典データセット
uspto-grants-2012_03
特許番号
US08143251B2

反応ノート

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