Citric Acid → {4-[(2-phenyl-1H-indol-1-yl)methyl]phenyl}methanol
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.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[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]=1Participants
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 1.5 M diisobutylaluminum hydride toluene solution (13.5 mL, 20.3 mmol) was added dropwise to the solution. The solution was stirred under ice-cooling for 4 hr, and aqueous citric acid solution was added to the reaction solution. The mixture was extracted with ethyl acetate. The extract washed with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The 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. MS: m/z 314 (MH+).
Workup
- temperaturecooled
- temperaturecooling for 4 hr
- extractionThe mixture was extracted with ethyl acetate
- washThe extract washed with aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5230d62c3b7d4dc58a9d5940b529a50e
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07517910B2
Reaction notes
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