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

HRID 384435Notes

Reaction equation

HRID 384435 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-30aad7794a8849cfb9112ce4d3c55cb9
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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