Reaktion #52065

Reaktionsgleichung

(3-formyl-phenoxy)-acetic acid tert-butyl ester

NH2OH.HCl

pyridine

→

title compound

Ausbeute 91.2%

[3-(Hydroxyimino-methyl)-phenoxy]-acetic acid tert-butyl ester

Ausbeute 91.2%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe MeOH was removed in vacuo
2. 2
   workup.ADDITIONthe residue was diluted with EtOAc and 1N HCl
3. 3
   SonstigeThe layers were separated
4. 4
   Waschenthe aqueous solution was washed with EtOAc
5. 5
   TrocknenThe combined organic layers were dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo

Vorschrift

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).

Quelle