Water → HCID 17979060, compound

HRID 1354160Notes

Reaction equation

HRID 1354160 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([CH3:12])=[CH2:11])[N:5]=[CH:4][N:3]=1.[OH-].[Na+].O.[CH:16]([Cl:19])(Cl)[Cl:17]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2([CH3:12])[CH2:11][C:16]2([Cl:19])[Cl:17])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 17979087HCID 17979087, compound

Product 1

HCID 17979060HCID 17979060, compound

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

In 6.5 ml of chloroform was dissolved 0.6 g of 4-chloro-6-(2-methylallyloxy)pyrimidine, to which 0.02 g of benzyltriethylammonium chloride was added at 0° C. and 3.25 ml of a 50% sodium hydroxide solution was further added dropwise at the same temperature, followed by stirring at room temperature for 14 hours. The reaction mixture was then poured into water, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.23 g of 4-chloro-6- [(2,2-dichloro-1-methylcyclopropyl)methoxy]pyrimidine.

Workup

  1. extractionwas extracted three times with t-butyl methyl ether
  2. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aee9a2881a444a339c9f5213a67ad7aa
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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