تفاعل #562242

معادلة التفاعل

MeCN

LHMDS

37

trans-N-methoxy-N-methyl-2-phenylcyclopropane-1-carboxamide

→

trans-3-oxo-3-(2-phenylcyclopropyl)propanenitrile

المردود 51.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe resulting solution was stirred at −60° C. for 10 min
2. 2
   أخرىquenched with sat'd
3. 3
   استخلاصThe reaction mixture was extracted with EtOAc (3×1 L)
4. 4
   تجفيفthe combined organic layers were dried (Na2SO4)
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىThe crude residue was purified by SiO2 chromatography
8. 8
   غسيلeluting with EtOAc/petroleum ether (10 to 25% EtOAc)

الإجراء التجريبي

To a stirred solution of MeCN (208.3 mL) and THF (200 mL) at −60° C. under N2 was added dropwise 1M LHMDS in THF (1040 mL). The reaction mixture was stirred at −60° C. for 3 h, and 37 (62.5 g, 304.5 mmol, 1.00 equiv) was then added dropwise. The resulting solution was stirred at −60° C. for 10 min and then quenched with sat'd. aq. NH4Cl solution (400 mL). The reaction mixture was extracted with EtOAc (3×1 L), and the combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by SiO2 chromatography eluting with EtOAc/petroleum ether (10 to 25% EtOAc) to afford 28.5 g (51%) of trans-3-oxo-3-(2-phenylcyclopropyl)propanenitrile (39) as a light yellow oil.

المصدر