Sodium Hydroxide → HCID 18607467, compound

HRID 1199229Notes

Reaction equation

HRID 1199229 reaction equation
[CH3:1][C:2]1([CH3:20])[C@@H:4]([C:5]2[CH:6]=[N:7][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[N:9][CH:10]=2)[C@@H:3]1[C:15]([O:17]CC)=[O:16].[OH-].[Na+]>C(O)C.O>[CH3:1][C:2]1([CH3:20])[C@@H:4]([C:5]2[CH:6]=[N:7][C:8]([C:11]([CH3:12])([CH3:13])[CH3:14])=[N:9][CH:10]=2)[C@@H:3]1[C:15]([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70361321HCID 70361321, compound

Product 1

HCID 18607467HCID 18607467, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl trans-2,2-dimethyl-3-[2-(2-methyl-prop-2-yl)pyrimidin-5-yl]cyclopropane carboxylate (2.6 g) in ethanol (50 cm3) was mixed with a solution of sodium hydroxide (1.0 g) in water (50 cm3) and the mixture stirred at the ambient temperature for 5 hours. After removal of the bulk of the ethanol by evaporation under reduced pressure the pH of the residual mixture was adjusted to 3 with dilute hydrochloric acid. The mixture was extracted with diethyl ether (2×200 cm3), and the combined extracts washed with water and dried over anhydrous magnesium sulphate. Evaporation of the ether under reduced pressure yielded trans-2,2-dimethyl-3-[2-(2-methylprop-2-yl)pyrimidin-5-yl]cyclopropane carboxylic acid (2.1 g), melting point 168°-9° C.

Workup

  1. customAfter removal of the bulk of the ethanol
  2. customby evaporation under reduced pressure the pH of the residual mixture
  3. extractionThe mixture was extracted with diethyl ether (2×200 cm3)
  4. washthe combined extracts washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customEvaporation of the ether under reduced pressure

Sources & evidence

ORD record
ord-ccdfd7dedfbb4226baf125624a6f2a64
Source dataset
uspto-grants-1990_02
Patent number
US04898968

Reaction notes

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