Ethanol → HCID 12503355, compound

HRID 1752296Notes

Reaction equation

HRID 1752296 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:15][CH2:16]O.O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([CH:15]=[CH2:16])=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 10340Sodium CarbonateHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 12503355HCID 12503355, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred mixture of 2-bromo-5-methyl-pyridine (1.7 g, 10 mmol), 2,4,6-trivinyl-cyclotriboroxanein (1.20 g, 5 mmol) and Na2CO3 (3.73 g, 35.2 mmol) in toluene (15 mL)/EtOH (10 mL)/H2O (5 mL) was added Pd(PPh3)4 (300 mg, 0.25 mmol) under N2. The mixture was stirred at 100° C. overnight. The resulting mixture was quenched with water (20 mL) and extracted with EtOAc (30 mL×3). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated. The residue was purified by chromatography column (PE:EA=50:1) to afford 5-methyl-2-vinyl-pyridine (900 mg, 75.6%) as a yellow oil.

Workup

  1. customThe resulting mixture was quenched with water (20 mL)
  2. extractionextracted with EtOAc (30 mL×3)
  3. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography column (PE:EA=50:1)

Sources & evidence

ORD record
ord-aa490b484ddf48cc9ab174a0561ae377
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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