Diisopropylamine → HCID 11630726、化合物

HRID 1663057ノート

反応式

HRID 1663057 の反応式
C(NC(C)C)(C)C.[Li]CCCC.[CH3:13][N:14]([CH3:27])[C:15]1[CH:16]=[CH:17][C:18]([CH3:26])=[C:19]([CH:25]=1)[C:20]([N:22]([CH3:24])C)=[O:21].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)C#N>C1COCC1>[CH3:27][N:14]([CH3:13])[C:15]1[CH:25]=[C:19]2[C:18]([CH:26]=[C:24]([C:36]3[CH:35]=[CH:32][CH:31]=[C:30]([O:29][CH3:28])[CH:37]=3)[NH:22][C:20]2=[O:21])=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 737123-MethoxybenzonitrileHCID 148392265-(Dimethylamino)-N,N,2-trimethylbenzamideHCID 178418339Butyllithium

生成物 1

HCID 11630726HCID 11630726、化合物収率 20.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a solution of diisopropylamine (1.5 g, 15 mmol) in dry THF (10 mL) was added n-BuLi (6 mL of 2.5 M in hexane, 15 mmol) at −78° C. After 30 min, a solution of 5-dimethylamino-2,N,N-trimethylbenzamide (2.06 g, 10 mmol) in THF (15 mL) was added dropwise at −78° C., the red orange solution was stirred at the same temperature for 1 h. The solution of 3-methoxybenzonitrile (1.7 g, 13 mmol) in dry THF (10 mL) were added and the reaction mixture was stirred at −78° C. for 2 h. The reaction solution was quenched with water and extracted with ethyl acetate and dried over sodium sulfate. After removing the solvent, the residue was purified by column chromatography with n-hexane-ethyl acetate (3:1) to afford compound I as yellow solid (596 mg, 20%). 1H NMR (300 MHz, CDCl3) δ: 9.73 (s, 1H), 7.61 (s, 1H), 7.50 (d, J=8.7 Hz, 1H), 7.38 (m, 1H), 7.23-7.22 (m, 3H), 6.96 (m, 1H), 6.74 (s, 1H), 3.90 (s, 3H), 3.09 (s, 6H).

後処理

  1. stirringthe reaction mixture was stirred at −78° C. for 2 h
  2. customThe reaction solution was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customAfter removing the solvent
  6. customthe residue was purified by column chromatography with n-hexane-ethyl acetate (3:1)

出典と根拠

ORDレコード
ord-5b4c4fc6668c463c9ef4ed59cdfc8d9d
出典データセット
uspto-grants-2011_10
特許番号
US08034829B2

反応ノート

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