Methyl Acrylate → Methyl 3-(pyridin-3-yl)-4,5-dihydro-1,2-oxazole-5-carboxylate

HRID 2219079Notes

Reaction equation

HRID 2219079 reaction equation
C(N(CC)CC)C.[OH:8][N:9]=[C:10](Cl)[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20]>C(O)C>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:10]2[CH2:20][CH:19]([C:18]([O:22][CH3:23])=[O:21])[O:8][N:9]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 53404818N-Hydroxy-3-pyridinecarboximidoyl chloride

Product 1

HCID 3693251Methyl 3-(pyridin-3-yl)-4,5-dihydro-1,2-oxazole-5-carboxylateYield 98.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

) A solution of N,N-diethylethanamine (0.544 mol) in ethanol (600 ml) was added dropwise to a stirred suspension of N-hydroxy-3-pyridinecarboximidoyl chloride (0.259 mol) and methyl 2-propenoate (1.295 mol) in ethanol (1500 ml) over a period of 1 hour. The reaction mixture was stirred for 1 hour at RT. The reaction mixture was evaporated. The residue was mixed with diethyl ether and filtered. The organic layer was separated, washed three times with water, separated again, dried (MgSO4), filtered and left overnight. Partial crystallization occurred on overnight standing. The crystals were filtered and dried and the filtrate was evaporated, yielding 52.6 g (98%) of (±)-methyl 4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxylate (interm. 1).

Workup

  1. customThe reaction mixture was evaporated
  2. additionThe residue was mixed with diethyl ether
  3. filtrationfiltered
  4. customThe organic layer was separated
  5. washwashed three times with water
  6. customseparated again
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. waitleft overnight
  10. customPartial crystallization
  11. waitoccurred on overnight
  12. filtrationThe crystals were filtered
  13. customdried
  14. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-05b14d34e02f4270b7c39381557b316a
Source dataset
uspto-grants-2008_08
Patent number
US07414048B2

Reaction notes

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