Pyridine → HCID 820544, compound

HRID 415963Notes

Reaction equation

HRID 415963 reaction equation
[Li+].C[Si]([N-:6][Si](C)(C)C)(C)C.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:17][C:18](=[CH2:22])[C:19](Cl)=[O:20]>C1COCC1>[CH3:17][C:18](=[CH2:22])[C:19]([NH:6][C:14]1[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=1)=[O:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 13528Methacryloyl chlorideHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 820544HCID 820544, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiHMDS (1.0 N in THF, 23.6 mmoL, 24 mL) was added dropwise into pyridine (11.8 mmoL, 1.11 g) in THF (10 mL) at 0° C. After 10 min, 2-methyl-acryloyl chloride (11.8 mmoL, 1.43 mL) was added into the reaction at 0° C. The reaction was then slowly warmed to room temperature. The solvent was removed and the residue was partitioned between Et2O and water. The Et2O layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The crude material (the brown oil) was then purified by column chromatography (silica gel, EtOAc as eluent) to yield the title compound as a reddish oil.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between Et2O and water
  3. washThe Et2O layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a brown oil
  8. customThe crude material (the brown oil) was then purified by column chromatography (silica gel, EtOAc as eluent)

Sources & evidence

ORD record
ord-fd03a78f0183478ab990e9a3d9dfaab5
Source dataset
uspto-grants-2012_01
Patent number
US08088811B2

Reaction notes

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