Triethylamine → HCID 11052524、化合物

HRID 1861779ノート

反応式

HRID 1861779 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 11052524HCID 11052524、化合物収率 78%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-28b55d320e9b40808279251badb3795b
出典データセット
uspto-grants-2003_03
特許番号
US06534522B2

反応ノート

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