Citric Acid → {4-[(2-phenyl-1H-indol-1-yl)methyl]phenyl}methanol

HRID 507908Notes

Reaction equation

HRID 507908 reaction equation
[C:1]1([C:7]2[N:8]([CH2:16][C:17]3[CH:26]=[CH:25][C:20]([C:21](OC)=[O:22])=[CH:19][CH:18]=3)[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.C1(C)C=CC=CC=1>[C:1]1([C:7]2[N:8]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([CH2:21][OH:22])=[CH:25][CH:26]=3)[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 21225700DiisobutylaluminumhydrideHCID 23111749methyl 4-[(2-phenyl-1H-indol-1-yl)methyl]benzoate

Product 1

HCID 23111705{4-[(2-phenyl-1H-indol-1-yl)methyl]phenyl}methanolYield 88%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-[(2-phenyl-1H-indol-1-yl)methyl]benzoate (2.8 g, 8.20 mmol) was dissolved in anhydrous tetrahydrofuran (100 mL), and the solution was ice-cooled. To this solution was added dropwise a solution (13.5 mL, 20.3 mmol) of 1.5 mol/L diisobutylaluminum hydride in toluene. This solution was stirred under ice-cooling for 4 hr. An aqueous citric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4-1:2) to give the title compound (2.25 g, yield 88%) as a colorless oil.

Workup

  1. temperaturecooled
  2. temperaturecooling for 4 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-36b2f64ca19f4457a36d3c81de79d001
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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