1,2-Dimethoxyethane → HCID 74888736, compound

HRID 2037311Notes

Reaction equation

HRID 2037311 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.CO[CH2:12][CH2:13]OC>C([O-])([O-])=O.[K+].[K+].C(OCC)C.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>[Cl:9][C:4]1[N:3]=[C:2]([CH:12]=[CH2:13])[CH:7]=[C:6]([CH3:8])[CH:5]=1

Participants

6

Reactant 2

HCID 80711,2-DimethoxyethaneHCID 108989972,6-Dichloro-4-methylpyridine

Product 1

HCID 74888736HCID 74888736, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,6-dichloro-4-methyl-pyridine (2.34 g, 14.4 mmol) and 2,4,6-trivinyl-cyclotriboroxane pyridine complex (1.75 g, 7.26 mmol) in DME (27 mL), 2 M aq. K2CO3 solution (10 mL) is added. The mixture is degassed and put under argon before Pd(PPh3)4 (300 mg, 0.26 mmol) is added. The mixture is stirred at 80° C. for 3 h before it is cooled to rt, diluted with diethyl ether and washed with sat. aq. NaHCO3 solution. The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1. The thus obtained product is dissolved in EA, repeatedly washed with 5% aq. citric acid solution, dried over MgSO4, filtered and evaporated to give 6-chloro-4-methyl-2-vinyl-pyridine (1.24 g) as a colourless oil; LC-MS: tR=0.90 min, [M+1]+=154.03.

Workup

  1. customThe mixture is degassed
  2. additionis added
  3. temperatureis cooled to rt
  4. washwashed with sat. aq. NaHCO3 solution
  5. extractionextract
  6. dry with materialis dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1
  10. dissolutionThe thus obtained product is dissolved in EA
  11. washrepeatedly washed with 5% aq. citric acid solution
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. customevaporated

Sources & evidence

ORD record
ord-dce2822a1e544f79b9787c44b76642ec
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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