Vinyl Acetate → HCID 58128508, compound

HRID 1798817Notes

Reaction equation

HRID 1798817 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[N:8][CH:9]=1)=[N+:2]=[N-:3].[C:20](OC=C)(=O)[CH3:21]>>[N:1]1([C:4]2[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[N:8][CH:9]=2)[CH:21]=[CH:20][N:3]=[N:2]1

Participants

3

Reactant 2

HCID 7904Vinyl AcetateHCID 58128600HCID 58128600, compound

Product 1

HCID 58128508HCID 58128508, compound

Conditions

Temperature
100 °C

Procedure

5-Azido-2-(4′-methoxybenzyloxy)pyridine from step 2 of this example (55 mg, 0.215 mmol) and vinyl acetate (692 μl, 7.51 mmol) were mixed in a flame dried high pressure sealable vessel. The reaction vessel was evacuated and charged with nitrogen, sealed, and heated to 100° C. for 15 hours. The reaction was cooled to room temperature and TLC indicated that the reaction was complete. Minimal dichloromethane was added to the reaction (just enough to dissolve solids that formed upon cooling) and the solution added to a Biotage 25 g SiO2 column, eluting with 20-50% ethyl acetate/heptane to give the title compound as a white solid.

Workup

  1. customdried high pressure sealable vessel
  2. customThe reaction vessel was evacuated
  3. additioncharged with nitrogen
  4. customsealed
  5. temperatureThe reaction was cooled to room temperature
  6. additionMinimal dichloromethane was added to the reaction (just enough
  7. dissolutionto dissolve solids that
  8. customformed
  9. temperatureupon cooling) and the solution
  10. washeluting with 20-50% ethyl acetate/heptane

Sources & evidence

ORD record
ord-53fdbac29007444b8702472c55aeb6b8
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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