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

HRID 2090682Notes

Reaction equation

HRID 2090682 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-a710330159ed402bacb604093ebef5f1
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

Loading…