Sodium Hydroxide → 2-{4-(1-Decenyl)-phenyl}-5-(6-hydroxy-1-heptenyl)-pyrimidine

HRID 725686Notes

Reaction equation

HRID 725686 reaction equation
[CH:1]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:22]=[CH:21][C:20](OS(C(F)(F)F)(=O)=O)=[CH:19][N:18]=2)=[CH:13][CH:12]=1)=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Na+].[OH:33][CH:34]([CH3:43])[CH2:35][CH2:36][CH2:37]/[CH:38]=[CH:39]/B(O)O>O1CCCC1>[CH:1]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:22]=[CH:21][C:20]([CH:39]=[CH:38][CH2:37][CH2:36][CH2:35][CH:34]([OH:33])[CH3:43])=[CH:19][N:18]=2)=[CH:13][CH:12]=1)=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 19352669E-6-hydroxy-1-heptenyldihydroxyboraneHCID 537310942-{4-(1-Decenyl)-phenyl}-5-trifluoromethylsulfonyloxypyrimidine

Product 1

HCID 541012492-{4-(1-Decenyl)-phenyl}-5-(6-hydroxy-1-heptenyl)-pyrimidineYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

After replacing the inner atmosphere of a four-necked flask equipped with a stirring device and a thermometer with nitrogen gas, the flask was charged with 1.0 g (2.26 mmol) of the 2-{4-(1-decenyl)-phenyl}-5-trifluoromethylsulfonyloxypyrimidine obtained above. Then, 0.01 g (0.008 mmol) of tetrakis-triphenylphosphine-palladium, 0.27 g (6.78 mmol) of sodium hydroxide and 20 ml of tetrahydrofuran were added thereto. Further, 19.5 ml of a solution prepared by dissolving 3.39 mmol of E-6-hydroxy-1-heptenyldihydroxyborane, prepared in the same manner as in Example 4, in tetrahydrofuran was dropwise added thereto at room temperature. The whole mixture was heated under reflux with stirring for 8 hours, and cooled to room temperature. After extraction with 30 ml of toluene, the organic layer was twice washed with each 10 ml portion of saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography to obtain 0.63 g (yield 69%) of 2-{4-(1-decenyl)-phenyl}-5-(6-hydroxy-1-heptenyl)-pyrimidine.

Workup

  1. customequipped with a stirring device
  2. customobtained above
  3. additionwas dropwise added
  4. customat room temperature
  5. temperatureThe whole mixture was heated
  6. temperatureunder reflux
  7. extractionAfter extraction with 30 ml of toluene
  8. washthe organic layer was twice washed with each 10 ml portion of saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationAfter distilling off the solvent
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-784c69aee95143a9ab75fe37cba2afdb
Source dataset
uspto-grants-1998_01
Patent number
US05707547

Reaction notes

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