Potassium Carbonate → 4-Methoxy-5-methyl-2-vinyl-pyridine

HRID 1908812Notes

Reaction equation

HRID 1908812 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH3:10])=[CH:4][N:3]=1.B1(C=C)OB([CH:17]=[CH2:18])OB(C=C)O1.C1C=CN=CC=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.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>[CH3:9][O:8][C:6]1[C:5]([CH3:10])=[CH:4][N:3]=[C:2]([CH:17]=[CH2:18])[CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 790022772-Chloro-4-methoxy-5-methylpyridine

Product 1

HCID 670271894-Methoxy-5-methyl-2-vinyl-pyridineYield 62.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-4-methoxy-5-methyl-pyridine (2.91 g, 18.5 mmol) in DME (75 mL), 2,4,6-trivinylcyclotriboroxane pyridine complex (3.13 g, 13.0 mmol) followed by 2 M aq. K2CO3 solution (25 mL) is added. The mixture is degassed and put under argon before Pd(PPh3)4 (384 mg, 0.332 mmol) is added. The mixture is stirred at 80° C. for 15 h before it is cooled to rt, diluted with water and extracted with diethyl ether. The org. extract is washed with sat. aq. NaHCO3 solution, dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 4-methoxy-5-methyl-2-vinyl-pyridine (1.22 g) as a white solid; LC-MS: tR=0.52 min, [M+1]+=150.08.

Workup

  1. additionis added
  2. customThe mixture is degassed
  3. additionis added
  4. temperatureis cooled to rt
  5. extractionextracted with diethyl ether
  6. extractionextract
  7. washis washed with sat. aq. NaHCO3 solution
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

Sources & evidence

ORD record
ord-ca2ada2e64134ac2912c9f7c0ff006f3
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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