Dimethylcarbamoyl Chloride → Tert-butyl 3-(6-cyano-2-pyridyl)propanoate

HRID 748150ノート

反応式

HRID 748150 の反応式
[O-][N+:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C[Si]([C:21]#[N:22])(C)C.CN(C)C(Cl)=O.C(OCC)(=O)C>[N+](CC)([O-])=O.O>[C:21]([C:7]1[N:2]=[C:3]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:4]=[CH:5][CH:6]=1)#[N:22]

参加物

7

反応物 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8857Ethyl AcetateHCID 82115Trimethylsilyl cyanideHCID 22939454HCID 22939454、化合物

生成物 1

HCID 22939301Tert-butyl 3-(6-cyano-2-pyridyl)propanoate収率 82.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6587Nitroethane溶媒

実験手順

tert-Butyl 3-(1-oxido-2-pyridyl)propanoate (0.88 g, 3.9 mmol) was dissolved in nitroethane (5 ml). Trimethylsilyl cyanide (0.78 g, 7.9 mmol) and N,N-dimethylcarbamoyl chloride (0.85 g, 7.9 mmol) were added thereto. The reaction mixture was stirred at room temperature for 48 hrs, combined with ethyl acetate and water. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was subjected to a silica gel (50 g) column chromatography and eluted with hexane-ethyl acetate (3:1, v/v) to give the titled compound (0.75 g, 82%). 1H-NMR (CDCl3) δ: 1.42 (9H, s), 2.74 (2H, t, J=7.1 Hz), 3.12 (2H, t, J=7.1 Hz), 7.41 (1H, d, J=7.8 Hz), 7.52 (1H, d, J=7.8 Hz), 7.72 (1H, t, J=7.8 Hz).

後処理

  1. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. washeluted with hexane-ethyl acetate (3:1

出典と根拠

ORDレコード
ord-c089b007d12e43a793e63be120163dff
出典データセット
uspto-grants-2008_07
特許番号
US07399759B2

反応ノート

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