Water → [5-(2,6-difluorophenyl)-1H-pyrrol-3-yl]methanol

HRID 2197147Notes

Reaction equation

HRID 2197147 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:13][CH:12]=[C:11]([C:14](OCC)=[O:15])[CH:10]=1.[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C.S([O-])([O-])(=O)=O.[Mg+2]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:13][CH:12]=[C:11]([CH2:14][OH:15])[CH:10]=1

Participants

8

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 66974572ethyl 5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 66974511[5-(2,6-difluorophenyl)-1H-pyrrol-3-yl]methanolYield 97%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 24083Sulfuric acid magnesium salt (1:1)Solvent

Procedure

A solution (35 mL) of ethyl 5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylate (3.35 g) in tetrahydrofuran was cooled to −50° C., and a 1.5 mol/L solution (30 mL) of diisobutylaluminum hydride in toluene was added dropwise by small portions. The mixture was stirred at the same temperature for 1 hr, water was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate, celite and anhydrous magnesium sulfate were added and the mixture was further stirred for 15 min. The suspension was filtrated, and the obtained filtrate was concentrated under reduced pressure to give the title compound as pale-red crystals (yield 2.70 g, 97%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. additionwere added
  3. stirringthe mixture was further stirred for 15 min
  4. filtrationThe suspension was filtrated
  5. concentrationthe obtained filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-241cb190d85842f58ccbf584663548d1
Source dataset
uspto-grants-2012_12
Patent number
US08338462B2

Reaction notes

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