Pyridine → HCID 89851745, compound

HRID 1771430Notes

Reaction equation

HRID 1771430 reaction equation
[OH:1][CH:2]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])[C:3]([O:5][CH2:6][CH3:7])=[O:4].N1C=CC=CC=1.[C:25](Cl)(=[O:27])[CH3:26]>CN(C)C1C=CN=CC=1.CCCCCCC>[C:25]([O:1][CH:2]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 89851533HCID 89851533, compound

Product 1

HCID 89851745HCID 89851745, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8900HeptaneSolvent

Procedure

The solution of ethyl glyoxate (50% toluene sol, 11.66 ml) and 2-methoxybenzeneethano (12.73 ml) were stirred for 1 hr to yield ethyl 2-hydroxy-2-(2-methoxyphenethoxy)acetate. The formation of ethyl 2-hydroxy-2-(2-methoxyphenethoxy)acetate was detected by 1H NMR and the reaction mixture was cooled with ice-bath and treated with pyridine (48.4 ml), 4-dimethylaminopyridine (0.44 g), and acetyl chloride (12.85 ml). After stirring under +7° C. for 1 hr, heptane (50 ml) was added, and the ice-bath cooling was removed to let the reaction mixture reach ambient temperature followed by filtration. The filtare was washed with MTBE (3×50 ml), and the combined solvents were washed with NaHCO3 (sat aq sol), water and NaCl (sat aq sol), dried over Na2SO4, and filtered. Organics were evaporated, toluene added and evaporated. By-products and residual solvents were distilled of (0 mbar-1 mbar/72°-105° C.), and the residual was dissolved in ethyl acetate. Silica gel and active carbon were added, the solution stirred for 10 min, and filtered. Organics were evaporated to yield ethyl 2-acetoxy-2-(2-methoxyphenethoxy)acetate (12.3 g) which was used in the next step.

Workup

  1. temperaturethe reaction mixture was cooled with ice-bath
  2. customwas removed
  3. customreach ambient temperature
  4. filtrationfollowed by filtration
  5. washThe filtare was washed with MTBE (3×50 ml)
  6. washthe combined solvents were washed with NaHCO3 (sat aq sol), water and NaCl (sat aq sol)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customOrganics were evaporated
  10. additiontoluene added
  11. customevaporated
  12. distillationBy-products and residual solvents were distilled of (0 mbar-1 mbar/72°-105° C.)
  13. dissolutionthe residual was dissolved in ethyl acetate
  14. additionSilica gel and active carbon were added
  15. stirringthe solution stirred for 10 min
  16. filtrationfiltered
  17. customOrganics were evaporated

Sources & evidence

ORD record
ord-a0a026f94ab44cc5a3a547465f2e1b9f
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

Loading…