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

HRID 1163304Notes

Reaction equation

HRID 1163304 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 mixture was ice-cooled. A solution (13.5 mL, 20.3 mmol) of 1.5 mol/L diisobutylaluminum hydride in toluene was added dropwise to the solution. This solution was stirred under ice-cooling for 4 hr, and 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 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-761f980f2a1c45e98c68fb72fd40bbe6
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

Loading…