Triethylamine → HCID 11052524, 화합물

HRID 1861779노트

반응식

HRID 1861779 반응식
[CH2:1]([C:8]1[CH:13]=[CH:12][N+:11]([O-])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[CH2:16][N:17](CC)CC.C[Si](C#N)(C)C>C(#N)C.C(Cl)Cl>[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:16]#[N:17])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 3155894-Benzyl-1-oxo-1lambda~5~-pyridine

생성물 1

HCID 11052524HCID 11052524, 화합물수율 78%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-benzylpyridine-N-oxide (8.8 g, 48 mmol) in acetonitrile (50 mL) was added Et3N (9.9 mL, 71.2 mmol). Neat trimethylsilyl cyanide (15.8 mL, 118 mmol) was added dropwise. The resulting solution was heated at reflux for 10 h under nitrogen then after cooling, diluted with CH2Cl2 (150 mL). The resulting solution was washed with NaHCO3 (2×150 mL), dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by filtration on silica gel using EtOAc/n-hexane as eluant to afford the title compound as a pale yellow oil (7.2 g, 78%): 1H NMR (CDCl3) δ4.03 (s, 2H), 7.16 (d, J=7.2 Hz, 2H), 7.20-7.40 (m, 4H), 7.49 (s, 1H), 8.59 (d, J=5.1 Hz, 1H); IR (film) 2240, 1600, 1500 cm−1.

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 10 h under nitrogen
  3. temperatureafter cooling
  4. washThe resulting solution was washed with NaHCO3 (2×150 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. filtrationThe crude compound was purified by filtration on silica gel

출처 및 근거

ORD 기록
ord-28b55d320e9b40808279251badb3795b
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06534522B2

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