Acrylonitrile → Dimethyl 2-(2-cyanoethyl)-2-(2-fluoro-4-nitrophenyl)malonate

HRID 1192875노트

반응식

HRID 1192875 반응식
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH:11]([C:16]([O:18][CH3:19])=[O:17])[C:12]([O:14][CH3:15])=[O:13].[C:20](#[N:23])[CH:21]=[CH2:22].C[O-].[Na+]>CO.ClCCl>[C:20]([CH2:21][CH2:22][C:11]([C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1])([C:16]([O:18][CH3:19])=[O:17])[C:12]([O:14][CH3:15])=[O:13])#[N:23]

참가 물질

6

반응물 3

HCID 7855AcrylonitrileHCID 10942334Sodium MethoxideHCID 53429620Dimethyl 2-(2-fluoro-4-nitrophenyl)malonate

생성물 1

HCID 86630008Dimethyl 2-(2-cyanoethyl)-2-(2-fluoro-4-nitrophenyl)malonate수율 52.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of the nitro diester, Dimethyl 2-(2-fluoro-4-nitrophenyl)malonate (86) (0.4 g, 1.47 mmol) and acrylonitrile (0.11 mL, 1.62 mmol) in absolute methanol (5 mL) was added a catalytic amount of sodium methoxide at 21° C. under argon. The reaction mixture was stirred for 40 h at the same temperature and then diluted with dichloromethane (50 mL). The resulting mixture was washed with water, brine and dried. The residue obtained upon evaporation of the solvents was purified on a silica gel (hexane:ethyl acetate, 8:1) to give Dimethyl 2-(2-cyanoethyl)-2-(2-fluoro-4-nitrophenyl)malonate (73) (0.25 g, 52%): 1H NMR δ 8.07 (dd, 1H, J=8.7, 2.3 Hz), 7.99 (dd, 1H, J=10.9, 2.3 Hz), 7.47 (dd, 1H, J=8.7, 7.3 Hz), 3.85 (s, 6H), 2.65-2.70 (m, 2H), 2.47-2.51 (m, 2H).

후처리

  1. washThe resulting mixture was washed with water, brine
  2. customdried
  3. customThe residue obtained upon evaporation of the solvents
  4. customwas purified on a silica gel (hexane:ethyl acetate, 8:1)

출처 및 근거

ORD 기록
ord-d7a87548317d4d01acc6c819988c0cdb
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680291B2

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