Cesium carbonate → HCID 86732291, compound

HRID 930489Notes

Reaction equation

HRID 930489 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[N:6][C:7]=1[CH:8]=[CH2:9].Br[CH2:12][C:13]#[C:14][CH3:15].[Na].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:12]([O:10][C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([CH:8]=[CH2:9])=[N:6][CH:5]=1)[C:13]#[C:14][CH3:15]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 74888431HCID 74888431, compoundHCID 86732292HCID 86732292, compound

Product 1

HCID 86732291HCID 86732291, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A reaction mixture of 5-methyl-6-vinylpyridin-3-ol (100 mg, 0.00074 mmol), sodium 1-bromobut-2-yne (118 mg, 0.00088 mol, Alfa-Aesar) and cesium carbonate (361 mg, 0.0011 mol) in DMF (2 mL) was stirred for 2 h at 80° C. After completion of the reaction, reaction mixture was cooled to ambient temperature, poured into ice-cold water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude residue was purified by column chromatography using silica gel and eluting with 0-10% ethyl acetate in petroleum ether to give 5-(but-2-yn-1-yloxy)-3-methyl-2-vinylpyridine as an off white solid (85 mg, 61.5%). MS m/z=188.3 [M+H]+.

Workup

  1. customAfter completion of the reaction, reaction mixture
  2. temperaturewas cooled to ambient temperature
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by column chromatography
  8. washeluting with 0-10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-c387574c9ae24a7ebce08f068c88dae5
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

Loading…