Acetic Anhydride → Acetic acid 5-phenoxy-pyridin-2-ylmethyl ester

HRID 78104Notes

Reaction equation

HRID 78104 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][N+:3]=1[O-].[C:16]([O:19]C(=O)C)(=[O:18])[CH3:17]>>[O:8]([C:5]1[CH:6]=[CH:7][C:2]([CH2:1][O:19][C:16](=[O:18])[CH3:17])=[N:3][CH:4]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 14044044HCID 14044044, compound

Product 1

HCID 66707652Acetic acid 5-phenoxy-pyridin-2-ylmethyl ester

Procedure

A mixture of 2-methyl-5-phenoxy-pyridine (3.6 g, 19 mmol) described in Manufacturing Example 121-1-1,3-chloroperoxybenzoic acid (5.6 g, 33 mmol), and methylene chloride (80 mL) was stirred at room temperature for 45 minutes. Aqueous sodium sulfite was added to the reaction solution, and the organic layer was separated and was washed with 5 N aqueous sodium hydroxide (7 mL). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under a reduced pressure to obtain 2-methyl-5-phenoxy-pyridine 1-oxide (3.3 g). 2-methyl-5-phenoxy-pyridine 1-oxide (3.3 g, 16 mmol) and acetic anhydride (20 mL) were stirred for 40 minutes at 115° C. Acetic anhydride was evaporated under a reduced pressure, aqueous sodium bicarbonate and ethyl acetate were added to the residue, and the organic layer was separated. The ethyl acetate solution was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane: ethyl acetate=2:1) to obtain an acetic acid 5-phenoxy-pyridin-2-ylmethyl ester (3.0 g). Acetic acid 5-phenoxy-pyridin-2-ylmethyl ester (3.0 g, 12 mmol), 5 N aqueous sodium hydroxide (8.0 mL), and methanol (20 mL) were stirred for 20 minutes at 60° C. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under a reduced pressure to obtain the title compound (2.6 g, 65%).

Workup

  1. customAcetic anhydride was evaporated under a reduced pressure, aqueous sodium bicarbonate and ethyl acetate
  2. additionwere added to the residue
  3. customthe organic layer was separated
  4. concentrationThe ethyl acetate solution was concentrated under a reduced pressure
  5. customthe residue was purified by silica gel column chromatography (heptane: ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5055d042609449a0bdee7c84c9bd07e4
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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