تفاعل #1574068

معادلة التفاعل

sodium hypochlorite

(E)-1-(3-(benzyloxy)-5-bromophenyl)-N-hydroxymethanimine

di-tert-butyl 2-methylenesuccinate

→

title compound

المردود 63.2%

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

المردود 63.2%

المذيبات

ethyl acetate

water

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   غسيلThe organic layer 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

An aqueous sodium hypochlorite solution (5%, 7.92 g) was added dropwise to a solution of (E)-1-(3-(benzyloxy)-5-bromophenyl)-N-hydroxymethanimine (1.48 g) and di-tert-butyl 2-methylenesuccinate (1.171 g) in THF (15 mL) at 0 C, and the obtained mixture was stirred at 0 C for 2 hours and subsequently at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, and water was added thereto. The organic layer 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 (1.67 g).

المصدر