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

HRID 384435ノート

反応式

HRID 384435 の反応式
[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

参加物

6

反応物 4

HCID 962WaterHCID 24436Sodium SulfateHCID 21225700Diisobutylaluminumhydride2 回HCID 59527045Ethyl 4-(benzyloxy)-8-methoxy-3-methylquinoline-2-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-30aad7794a8849cfb9112ce4d3c55cb9
出典データセット
uspto-grants-2013_02
特許番号
US08367702B2

反応ノート

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