Water → [4-(Benzyloxy)-8-methoxy-3-methylquinolin-2-yl]methanol

HRID 384435노트

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HRID 384435 반응식
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[C:14]([O:19][CH3:20])[CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([C:21](OCC)=[O:22])[C:10]=1[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[C:14]([O:19][CH3:20])[CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:21][OH:22])[C:10]=1[CH3:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24436Sodium SulfateHCID 21225700Diisobutylaluminumhydride2회HCID 59527045Ethyl 4-(benzyloxy)-8-methoxy-3-methylquinoline-2-carboxylate

생성물 1

HCID 59526840[4-(Benzyloxy)-8-methoxy-3-methylquinolin-2-yl]methanol수율 32.1%

시약·촉매·용매 1

HCID 1140Toluene용매3회

실험 절차

To a solution of ethyl 4-(benzyloxy)-8-methoxy-3-methylquinoline-2-carboxylate (1.95 g) in toluene (30 mL) was added dropwise a solution of diisobutylaluminum hydride in toluene (0.99M, 6.1 mL) at room temperature under nitrogen flow, followed by stirring. After 1 hour and 2 hours, a solution of diisobutylaluminum hydride in toluene (0.99M, each 6.1 mL) was added thereto, followed by stirring for 3 hours. Water was added to the reaction mixture to stop the reaction, and then anhydrous sodium sulfate was added thereto, followed by stirring. Insolubles were removed by filtration through Celite. The filtrate was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/50˜ethyl acetate, then chloroform˜chloroform/methanol=95/5) to obtain [4-(benzyloxy)-8-methoxy-3-methylquinolin-2-yl]methanol (551 mg).

후처리

  1. stirringby stirring for 3 hours
  2. customthe reaction
  3. stirringby stirring
  4. customInsolubles were removed by filtration through Celite
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent

출처 및 근거

ORD 기록
ord-30aad7794a8849cfb9112ce4d3c55cb9
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367702B2

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