Sodium Hydroxide → HCID 14718884, compound

HRID 1085712Notes

Reaction equation

HRID 1085712 reaction equation
[OH-].[Na+].[CH3:3][C:4]([C:7]1[N:12]=[CH:11][C:10]([C:13](=[C:19]([CH3:21])[CH3:20])[C:14]([O:16]CC)=[O:15])=[CH:9][N:8]=1)([CH3:6])[CH3:5]>C(O)(C)C.O>[CH3:6][C:4]([C:7]1[N:8]=[CH:9][C:10]([C:13](=[C:19]([CH3:21])[CH3:20])[C:14]([OH:16])=[O:15])=[CH:11][N:12]=1)([CH3:3])[CH3:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14718883HCID 14718883, compound

Product 1

HCID 14718884HCID 14718884, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of sodium hydroxide 0.24 g) and ethyl 2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3-methylbut-2-enoate (0.4 g) in isopropanol (10 cm3) and water (2 cm3) was heated to the reflux temperature for a period of 3 hours. After cooling to the ambient temperature the crude reaction mixture was concentrated by evaporation of the solvent under reduced pressure, and the residue was dissolved in water, and extracted with ethyl acetate. The aqueous portion was acidified with dilute hydrochloric acid, and extracted with ethyl acetate. The combined organic extracts were washed with water, dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvent under reduced pressure to give 2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3-methylbut-2-enoic acid, containing a small amount of 2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3-methylbut-3-enoic acid. The crude produce was used without further purification.

Workup

  1. customreaction mixture
  2. concentrationwas concentrated by evaporation of the solvent under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. concentrationconcentrated by evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-c76db4a086e54ba7b0f530a7b14017ef
Source dataset
uspto-grants-1991_04
Patent number
US05010200

Reaction notes

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