تفاعل #161154

معادلة التفاعل

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

المردود 52.0%

المذيبات

water

benzene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةat reflux overnight
3. 3
   أخرىthe organic layer was separated
4. 4
   استخلاصThe aqueous phase was extracted with EtOAc (300×3 mL)
5. 5
   غسيلThe combined organic layers were washed with brine
6. 6
   تجفيفdried over anhydrous Na2SO4
7. 7
   تركيزconcentrated
8. 8
   أخرىThe residue was purified by column chromatography

الإجراء التجريبي

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%).

المصدر