Water → (Quinolin-5-yl)methanol

HRID 633766노트

반응식

HRID 633766 반응식
[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

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 12503486Methyl quinoline-5-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 823080(Quinolin-5-yl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-15ef336b9597444780de8985a44941ef
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321790B2

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