2-Chlorocyclohexanol → HCID 22599838, compound

HRID 1592272Notes

Reaction equation

HRID 1592272 reaction equation
[H-].[Na+].[Cl:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[OH:10].[Cl:11][C:12]1[CH:17]=[C:16](Cl)[N:15]=[CH:14][N:13]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:11][C:12]1[CH:17]=[C:16]([O:10][CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH:4]2[Cl:3])[N:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 152742-ChlorocyclohexanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 22599838HCID 22599838, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

In 4.7 ml of tetrahydrofuran was suspended 0.12 g of sodium hydride (60% in oil), to which 1 ml of a tetrahydrofuran solution containing 0.45 g of 2-chlorocyclohexanol was slowly added dropwise with stirring at 0° C. The mixture was stirred at 0° C. for 10 minutes, to which 1 ml of a tetrahydrofuran solution containing 0.5 g of 4,6-dichloropyrimidine was added at 0° C., followed by further stirring for 20 minutes. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with ethyl acetate. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.38 g of 4-chloro-6-(2-chlorocyclohexyloxy)pyrimidine.

Workup

  1. additionwas slowly added dropwise
  2. additionwas added at 0° C.
  3. stirringby further stirring for 20 minutes
  4. extractionextracted three times with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f69788b01f97411687736284bae1d9ce
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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