(Triphenylphosphoranylidene)acetonitrile → (E)-Methyl 4,5-dichloro-2-(2-cyanovinyl)benzoate

HRID 84937

반응식

HRID 84937 반응식
[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH:13]=O)[CH:3]=1.C1(P(=[CH:34][C:35]#[N:36])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4](/[CH:13]=[CH:34]/[C:35]#[N:36])[CH:3]=1

참가 물질

4

반응물 2

HCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 86647797Methyl 4,5-dichloro-2-formylbenzoate

생성물 1

HCID 86647796(E)-Methyl 4,5-dichloro-2-(2-cyanovinyl)benzoate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of the product from Example 56C (2.0 g, 8.6 mmol) and (triphenylphosphoranylidene)acetonitrile (2.87 g, 9.5 mmol) in toluene (30 mL) was refluxed for 24 hours. The reaction was cooled to room temperature and filtered through a short plug of silica gel eluting with diethyl ether to remove the triphenyl phosphine oxide. The filtrate was concentrated and the residue was purified via flash chromatography on a silica gel column (5:95 ethyl acetate:hexane) to afford the title compound and the corresponding Z isomer. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.88 (s, 3H) 6.55 (d, J=16.27 Hz, 1H) 8.05 (d, J=16.95 Hz, 1H) 8.09 (s, 1H) 8.13 (s, 1H); MS (DCI+) m/z 273.0 [M+H]+.

후처리

  1. temperaturewas refluxed for 24 hours
  2. filtrationfiltered through a short plug of silica gel eluting with diethyl ether
  3. customto remove the triphenyl phosphine oxide
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified via flash chromatography on a silica gel column (5:95 ethyl acetate:hexane)

출처 및 근거

ORD 기록
ord-6fbeb336356947ea9aa4ad3a0f377ec9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846951B2

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