Acetic Anhydride → HCID 20291313, compound

HRID 250969Notes

Reaction equation

HRID 250969 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N+:3]=1[O-].[CH3:16][C:17]([O:19]C(C)=O)=[O:18]>>[O:8]([C:7]1[C:2]([CH2:1][O:19][C:17](=[O:18])[CH3:16])=[N:3][CH:4]=[CH:5][CH:6]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 14044046HCID 14044046, compound

Product 1

HCID 20291313HCID 20291313, compoundYield 28%

Procedure

A solution of 2-methyl-3-phenoxy-pyridine 1-oxide (0.690 g, 3.40 mmol) in Ac2O (3.4 mL) stirred at 80° C. for 3 h. The solution was concentrated and the resulting residue was diluted with CH2Cl2 (30 mL). The organic layer was washed with saturated aqueous NaHCO3 (2×30 mL), dried (MgSO4), and concentrated. Purification by column chromatography on silica gel with hexanes/Et2O (1:1) afforded acetic acid 3-phenoxy-pyridin-2-ylmethyl ester as a clear oil (0.234 g, 28%). 1H NMR (CDCl3) δ 2.07 (s, 3H), 5.34 (s, 2H), 7.00 (d, 2H, J=8.0 Hz), 7.13-7.23 (m, 2H), 7.36 (m, 2H), 8.39 (dd, 1H, J=3.4, 2.1 Hz).

Workup

  1. concentrationThe solution was concentrated
  2. additionthe resulting residue was diluted with CH2Cl2 (30 mL)
  3. washThe organic layer was washed with saturated aqueous NaHCO3 (2×30 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel with hexanes/Et2O (1:1)

Sources & evidence

ORD record
ord-ee3037f401944df8a04daec4837fbcb6
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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