3-Hydroxy-3-methyl-2-butanone → HCID 68940191, compound

HRID 1798501Notes

Reaction equation

HRID 1798501 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:10]=O)[CH:7]=[N:8][CH:9]=1.[OH:12][C:13]([CH3:18])([CH3:17])[C:14](=[O:16])[CH3:15]>CO.CCOC(C)=O>[Br:3][C:4]1[CH:5]=[C:6](/[CH:10]=[CH:15]/[C:14](=[O:16])[C:13]([OH:12])([CH3:18])[CH3:17])[CH:7]=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 82613-Hydroxy-3-methyl-2-butanoneHCID 14798Sodium HydroxideHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 68940191HCID 68940191, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of sodium hydroxide (1.1 eq, 29.6 mmol, 29.6 ml) in MeOH (100 ml) under an inert atmosphere of nitrogen is cooled at 0° C. and treated with 5-bromo-pyridine-3-carbaldehyde (1 eq, 26.9 mmol, 5 g). After 1 h at 0° C., 3-hydroxy-3-methyl-butan-2-one (1 eq, 26.9 mmol, 2.75 g) is added and the reaction mixture is stirred at room temperature for 3 hours. The reaction mixture is dissolved in EtOAc and washed with water. The combined organic extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is purified by flash chromatography (0-50% EtOAc in iso-hexane) to afford the title compound; [M+H]+ 270/272.

Workup

  1. washwashed with water
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography (0-50% EtOAc in iso-hexane)

Sources & evidence

ORD record
ord-05d58c1332ed46ecad007758228a745b
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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