Water → (Quinolin-5-yl)methanol

HRID 633766ノート

反応式

HRID 633766 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:17](OC)=[O:18])[C:11]=2[CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>C1COCC1>[N:7]1[C:16]2[C:11](=[C:12]([CH2:17][OH:18])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 12503486Methyl quinoline-5-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 823080(Quinolin-5-yl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A suspension of 171 mg (4.49 mmol) of lithium aluminum hydride in 20 ml of THF is cooled to 0° C. A solution of 700 mg (3.74 mmol) of methyl quinoline-5-carboxylate in 5 ml of THF is then added dropwise. The reaction mixture is stirred at 0° C. for 1 hour and then hydrolysed with, in this order, 0.17 ml of H2O, 0.17 ml of NaOH and 3×0.17 ml of H2O. The precipitate formed is filtered off and washed with THF and then with EtOAc. The organic phase is washed with saturated NaCl solution, dried and evaporated. After purification by chromatography on silica gel (eluent: 95/5 DCM/MeOH), 190 mg of quinolin-5-ylmethanol are obtained, corresponding to the following characteristics:

後処理

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. washwashed with THF
  4. washThe organic phase is washed with saturated NaCl solution
  5. customdried
  6. customevaporated
  7. customAfter purification by chromatography on silica gel (eluent: 95/5 DCM/MeOH), 190 mg of quinolin-5-ylmethanol
  8. customare obtained, corresponding to the following characteristics

出典と根拠

ORDレコード
ord-15ef336b9597444780de8985a44941ef
出典データセット
uspto-grants-2016_04
特許番号
US09321790B2

反応ノート

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