تفاعل #1574073

معادلة التفاعل

tert-butyl 3-(5-(benzyloxy)-2-bromophenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

benzyl acrylate

tris(2-methylphenyl)phosphine

triethylamine

→

title compound

المردود 22.6%

tert-Butyl 3-(5-(benzyloxy)-2-((1E)-3-(benzyloxy)-3-oxoprop-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

المردود 22.6%

المذيبات

water

DMF

ظروف التفاعل

المعالجة

1. 1
   استخلاصfollowed by extraction with ethyl acetate
2. 2
   غسيلThe extract was washed with brine
3. 3
   تجفيفdried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
5. 5
   أخرىThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

الإجراء التجريبي

A mixture of tert-butyl 3-(5-(benzyloxy)-2-bromophenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (1.00 g), benzyl acrylate (1.484 g), palladium acetate (0.021 g), tris(2-methylphenyl)phosphine (0.084 g), triethylamine (0.765 mL), and DMF (10 mL) was stirred at 100 C for 2 days in an argon atmosphere. To the reaction mixture, water was added, followed by extraction with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (0.260 g).

المصدر