Allyl Alcohol → HCID 61277132, compound

HRID 2194420Notes

Reaction equation

HRID 2194420 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH2:9]([OH:12])[CH:10]=[CH2:11].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH2:9]([O:12][C:6]1[CH:7]=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1)[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 10796Cesium carbonateHCID 709434,6-Dichloropyrimidine

Product 1

HCID 61277132HCID 61277132, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 7.5 g (50.3 mmol) of 4,6-dichloropyrimidine and 3.61 ml (3.07 g, 52.9 mmol) of allyl alcohol in 40 ml of dioxane were added 19.6 g (60.4 mmol) of cesium carbonate. The suspension was stirred for 14 h at 85° C. and then allowed to cool to room temperature. The solution was filtered, and the salts were washed with ethyl acetate. The filtrate was concentrated in vaccuo and purified by flash chromatography on silicagel using ethyl acetate as eluant to yield 4.42 g (25.9 mmol, 51%) of the title compound as a colorless oil.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe solution was filtered
  3. washthe salts were washed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vaccuo
  5. custompurified by flash chromatography on silicagel

Sources & evidence

ORD record
ord-38b07444ae1c4beca65cb618b8a7415b
Source dataset
uspto-grants-2012_12
Patent number
US08334287B2

Reaction notes

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