تفاعل #1574055

معادلة التفاعل

sodium hypochlorite

(E)-1-(5-(benzyloxy)-2-bromophenyl)-N-hydroxymethanimine

di-tert-butyl 2-methylenesuccinate

→

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

المردود 82.1%

title compound

المردود 82.1%

المذيبات

ethyl acetate

hydrochloric acid

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%, 16.42 g) was added dropwise to a solution of (E)-1-(5-(benzyloxy)-2-bromophenyl)-N-hydroxymethanimine (3.07 g) and di-tert-butyl 2-methylenesuccinate (2.43 g) in THF (30 mL) at 0 C, and the obtained mixture was stirred at 0 C for 2 hours. The reaction mixture was diluted with ethyl acetate, and 1 M hydrochloric acid 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 (4.50 g).

المصدر