Sodium Carbonate → HCID 18759616, compound

HRID 432554Notes

Reaction equation

HRID 432554 reaction equation
[CH2:1]([Si:4]([CH2:18][CH:19]=[CH2:20])([CH3:17])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1)[CH:2]=[CH2:3].Br[C:22]1[C:35]2[C:26](=[C:27]3[C:32](=[CH:33][CH:34]=2)[C:31]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:30][CH:29]=[N:28]3)[N:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].O.CO>C1(C)C=CC=CC=1>[CH2:1]([Si:4]([CH2:18][CH:19]=[CH2:20])([CH3:17])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:22]2[C:35]3[C:26](=[C:27]4[C:32](=[CH:33][CH:34]=3)[C:31]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[CH:30][CH:29]=[N:28]4)[N:25]=[CH:24][CH:23]=2)=[CH:10][CH:9]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 18759597HCID 18759597, compound2×HCID 18759599HCID 18759599, compoundHCID 22242641Methanol--water (1/1)

Product 1

HCID 18759616HCID 18759616, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

4-{3-[diallyl(methyl)silyl]propyl}phenylboronic acid is made by the method of Casado and Stobart (Casado, M. A.; Stobart, S. R., Org. Lett., 2 (11), 2000, 1549-1552). 4-{3-[diallyl(methyl)silyl]propyl}phenylboronic acid (0.576 g) and a solution of Pd(Ph3)4 (58 mg) in 5 mL of degassed toluene is placed in a 50 mL Schlenk tube. The mixture is purged with nitrogen, after which a solution of 4-bromo-7-phenyl-1,10-phenanthroline (0.670 g) and Na2CO3 (428 mg, 4 mmol) in 5 mL of degassed 4:1 H2O/CH3OH is added. The mixture is heated under nitrogen at 100° C. with rapid stirring until TLC monitoring shows the reaction to be complete (ca 24 hrs). The reaction mixture is then added to a separatory funnel and washed with ether (3×50 mL). The combined organic fractions are dried over MgSO4 and concentrated by roto-evaporation. The desired product is purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane.

Workup

  1. customThe mixture is purged with nitrogen
  2. additionis added
  3. customthe reaction
  4. custom(ca 24 hrs)
  5. additionThe reaction mixture is then added to a separatory funnel
  6. washwashed with ether (3×50 mL)
  7. dry with materialThe combined organic fractions are dried over MgSO4
  8. concentrationconcentrated by roto-evaporation
  9. customThe desired product is purified by column chromatography on silica gel using
  10. additiona mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-b78f53c85c84454bbf8a957fb2d4eee3
Source dataset
uspto-grants-2003_12
Patent number
US06664111B2

Reaction notes

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