Water → (5-Phenyl-1H-pyrrol-3-YL)methanol

HRID 1782210Notes

Reaction equation

HRID 1782210 reaction equation
[C:1]1([C:7]2[NH:11][CH:10]=[C:9]([C:12](OCC)=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1.C1(C)C=CC=CC=1>[C:1]1([C:7]2[NH:11][CH:10]=[C:9]([CH2:12][OH:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10242379Ethyl 5-phenyl-1H-pyrrole-3-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 57179302(5-Phenyl-1H-pyrrol-3-YL)methanolYield 87%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution (100 mL) of ethyl 5-phenyl-1H-pyrrole-3-carboxylate (2.16 g) in tetrahydrofuran was cooled to −78° C., and a 1.5 mol/L solution (24 mL) of diisobutylaluminum hydride in toluene was added dropwise over 10 min. The mixture was further stirred at −78° C. for 1 hr, water (2 mL) was added dropwise over 2 min, and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was filtered using celite and anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound as a pale-red powder (yield 1.51 g, 87%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e620bb8c96c044ae89795f40aff01e3e
Source dataset
uspto-grants-2009_03
Patent number
US07498337B2

Reaction notes

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