반응 #2254202
ord-8317d059fb864abfb2301d43accd254c
반응 방정식
반응 조건
후처리
- 1기타A round bottom flask was equipped with a condenser, addition funnel
- 2온도while cooling the reaction flask in an ice bath
- 3추출The product was extracted with Et2O (3×50 ml)
- 4세척washed with brine (50 ml)
- 5기타dried (NA2SO4)
- 6농축concentrated
- 7기타Purified by normal phase SiO2 chromatography (7% to 60% EtOAc/hexanes)
실험 절차
A round bottom flask was equipped with a condenser, addition funnel and rubber septum with nitrogen inlet was charged with a solution of p-fluorophenylmagnesium bromide (2.0 M in diethyl ether, 1.99 ml, 3.97 mmol) and CuI (63 mg, 0.331 mmol) in 10 ml dry diethyl ether (10 ml). Methyl 2-cyano-2-(oxan-4-ylidene)acetate (600 mg, 3.31 mmol) in diethyl ether (10 ml) was added drop-wise over 30 min while cooling the reaction flask in an ice bath. The mixture was then stirred for 3 h. The reaction mixture was poured into a 50 g ice/1 N HCl (25 ml) mixture. The product was extracted with Et2O (3×50 ml), washed with brine (50 ml), dried (NA2SO4) and concentrated. Purified by normal phase SiO2 chromatography (7% to 60% EtOAc/hexanes) to give methyl 2-cyano-2-[4-(4-fluorophenyl)oxan-4-yl]acetate as a white solid (730 mg, 80%, m/z: 277.1 [M+Na]+ observed).