Reaktion #161154

Reaktionsgleichung

N-(3-hydroxy-phenyl)-acetamide

acetic acid 3-formylamino-phenyl ester

3-methyl-but-3-en-1-ol

DEAD

Ph3P

→

N-[3-(3-methyl-but-3-enyloxy)-phenyl]-acetamide

Ausbeute 52.0%

Lösungsmittel

water

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux overnight
3. 3
   Sonstigethe organic layer was separated
4. 4
   ExtraktionThe aqueous phase was extracted with EtOAc (300×3 mL)
5. 5
   WaschenThe combined organic layers were washed with brine
6. 6
   Trocknendried over anhydrous Na2SO4
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was purified by column chromatography

Vorschrift

A suspension of the mixture of N-(3-hydroxy-phenyl)-acetamide and acetic acid 3-formylamino-phenyl ester (18.12 g, 0.12 mol), 3-methyl-but-3-en-1-ol (8.6 g, 0.1 mol), DEAD (87 g, 0.2 mol) and Ph3P (31.44 g, 0.12 mol) in benzene (250 mL) was heated at reflux overnight and then cooled to room temperature. The reaction mixture was poured into water and the organic layer was separated. The aqueous phase was extracted with EtOAc (300×3 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to give N-[3-(3-methyl-but-3-enyloxy)-phenyl]-acetamide (11 g, 52%).

Quelle