Lithium Hydroxide → 131817-86-2

HRID 2371968Notes

Reaction equation

HRID 2371968 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([N:18]([O:20]C(=O)C)[CH3:19])=[O:17])=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[OH-].[Li+]>CC(O)C>[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([N:18]([OH:20])[CH3:19])=[O:17])=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 19905480HCID 19905480, compound

Product 1

HCID 6439321131817-86-2

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 3.12 g (E)-3-[4-(2,5-dimethyl-1-H-pyrrol-1-yl)phenyl]-N-acetoxy-N-methyl-2-propenamide in 2-propanol (50 ml) cooled to 0°, 1N aqueous lithium hydroxide (13 ml) is added with stirring. The mixture is stirred at room temperature for 30 minutes, then partitioned between ethyl acetate and 2N HCl. The organic phase is washed with brine, dried over magnesium sulphate and concentrated to dryness. Recrystallization from ethyl acetate yields (E)-3-[4-(2,5-dimethyl-1-H-pyrrol-1-yl)-phenyl]-N-hydroxy-N-methyl-2-propenamide of Example 1.

Workup

  1. stirringThe mixture is stirred at room temperature for 30 minutes
  2. custompartitioned between ethyl acetate and 2N HCl
  3. washThe organic phase is washed with brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-631b651f058a404da581e2d5ff5b1a7c
Source dataset
uspto-grants-1992_03
Patent number
US05096919

Reaction notes

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