Acetic Anhydride → (+)-1-[4-Methoxy-2-pyridyl]-ethyl acetate

HRID 1789060Notes

Reaction equation

HRID 1789060 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][N+:4]=1[O-])[CH3:2].[C:12]([O:15]C(=O)C)(=[O:14])[CH3:13]>>[C:12]([O:15][CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][N:4]=1)[CH3:2])(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic Anhydride2×HCID 543686382-Ethyl-4-methoxypyridine 1-oxide

Product 1

HCID 20189509(+)-1-[4-Methoxy-2-pyridyl]-ethyl acetateYield 78%

Conditions

Temperature
90 °C

Procedure

171 g of 2-ethyl-4-methoxy-pyridine N-oxide are added dropwise within 3 h to 312 ml of acetic anhydride heated to 90° C., in such a way that the internal temperature does not exceed 115° C. The mixture is then left to stand for a further 2.5 h at 100° C., and excess acetic anhydride is stripped off. Distillation of the residue gives 171 g (78%) of the title compound of b.p. 100° C./1 Pa.

Workup

  1. customdoes not exceed 115° C
  2. waitThe mixture is then left
  3. distillationDistillation of the residue

Sources & evidence

ORD record
ord-500050d121a64feabe3a407461393efa
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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