Methallyl alcohol → HCID 17979087, compound

HRID 1354159Notes

Reaction equation

HRID 1354159 reaction equation
[H-].[Na+].[CH3:3][C:4](=[CH2:7])[CH2:5][OH:6].[Cl:8][C:9]1[CH:14]=[C:13](Cl)[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:8][C:9]1[CH:14]=[C:13]([O:6][CH2:5][C:4]([CH3:3])=[CH2:7])[N:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 10557Methallyl alcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 17979087HCID 17979087, compoundYield 310%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 10 ml of tetrahydrofuran was suspended 0.322 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.16 g of 2-methyl-2-propenol in tetrahydrofuran was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of a solution containing 1 g of 4,6-dichloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, 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 1.27 g of 4-chloro-6-(2-methylallyloxy)pyrimidine.

Workup

  1. additionwas added dropwise at 0° C.
  2. stirringby stirring at the same temperature for 2 hours
  3. extractionwas extracted three times with t-butyl methyl ether
  4. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8e19d21a6ad34d03a00c19d018f3e433
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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