Pyridine → (3-(Hydroxyimino-methyl)-phenoxy)-acetic acid tert-butyl ester

HRID 23787Notes

Reaction equation

HRID 23787 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:18][OH:19].Cl.N1C=CC=CC=1>CO>[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[N:18][OH:19])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 14971816tert-Butyl (3-formylphenoxy)acetate

Product 1

HCID 73704862(3-(Hydroxyimino-methyl)-phenoxy)-acetic acid tert-butyl esterYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3-formyl-phenoxy)-acetic acid tert-butyl ester (2.05 g, 8.68 mmol) in MeOH (30 mL) was added NH2OH.HCl (0.66 g, 9.54 mmol) and pyridine (3.5 mL, 43.4 mmol) and the reaction was stirred for 2 hours. The MeOH was removed in vacuo and the residue was diluted with EtOAc and 1N HCl. The layers were separated and the aqueous solution was washed with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to afford the title compound (1.99 g). 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.23-7.28 (m, 2H), 7.12 (m, 1H), 6.93 (d, 1H), 4.51 (s, 2H), 1.46 (s, 9H).

Workup

  1. customThe MeOH was removed in vacuo
  2. additionthe residue was diluted with EtOAc and 1N HCl
  3. customThe layers were separated
  4. washthe aqueous solution was washed with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eb6bf27af57a4f06916935bd5ffd8774
Source dataset
uspto-grants-2005_02
Patent number
US06852863B2

Reaction notes

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