m-Formylbenzonitrile → 3-Ethenylbenzonitrile

HRID 496603노트

반응식

HRID 496603 반응식
[Li][CH2:2]CCC.[C:6]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)#[N:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:6]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[CH2:2])#[N:7]

참가 물질

5

반응물 2

HCID 90670m-FormylbenzonitrileHCID 178418339Butyllithium

생성물 1

HCID 2205433-Ethenylbenzonitrile수율 62.9%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred suspension of methyltriphenylphosphonium bromide (75 g, 209.71 mmol) in dry THF (750 mL) at 0° C. under nitrogen was added dropwise n-BuLi (83 mL, 2.5 M in hexanes, 207.50 mmol). The mixture was warmed to room temperature. 3-Cyanobenzaldehyde (25 g, 190.65 mmol) was added as a solid in 5 g batches, and the mixture was stirred at room temperature overnight. The reaction was quenched in water, and the solvent was removed under vacuum. The residue was dissolved in the minimal amount of THF, and triphenylphosphine oxide was precipitated using ether. The solid was filtered through diatomaceous earth, and the filtrate was concentrated. Distillation by Kugelrhor at 90° C./33 Pa (0.25 mm Hg) gave the product as a colorless oil (15.5 g, 62%).

후처리

  1. customThe reaction was quenched in water
  2. customthe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in the minimal amount of THF, and triphenylphosphine oxide
  4. customwas precipitated
  5. filtrationThe solid was filtered through diatomaceous earth
  6. concentrationthe filtrate was concentrated
  7. distillationDistillation by Kugelrhor at 90° C./33 Pa (0.25 mm Hg)

출처 및 근거

ORD 기록
ord-5319d6c445d948d4b259f206e53fe953
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06946467B2

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