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

HRID 378192노트

반응식

HRID 378192 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4d8c897cf4c1420ba01d80e24ab8dfd8
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06030546

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