Sodium hydride → tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-ethyloxetan-3-yl)prop-2-enoate

HRID 56873ノート

反応式

HRID 56873 の反応式
[H-].[Na+].[CH2:3]([C:5]1([CH:9]=O)[CH2:8][O:7][CH2:6]1)[CH3:4].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:35]#[N:36])=[C:16]([C:18]2[C:23]([O:24][CH3:25])=[CH:22][N:21]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:20](=[O:34])[CH:19]=2)[CH:17]=1>CN(C)C=O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:35]#[N:36])=[C:16]([C:18]2[C:23]([O:24][CH3:25])=[CH:22][N:21]([C:26](=[CH:9][C:5]3([CH2:3][CH3:4])[CH2:6][O:7][CH2:8]3)[C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[C:20](=[O:34])[CH:19]=2)[CH:17]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 534845673-Ethyloxetane-3-carbaldehydeHCID 117622654tert-Butyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate

生成物 1

HCID 118877902tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-ethyloxetan-3-yl)prop-2-enoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

38.4 mg (1.60 mmol, 2 eq., 60% in mineral oil) of sodium hydride and 457 mg (4.00 mmol) of 3-ethyloxetane-3-carbaldehyde in 1 ml of dimethylformamide were added in succession to a solution of 300 mg (800 μmol) of tert-butyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate in 8 ml of dimethylformamide. After 15 min at RT, the reaction was terminated by addition of 10 ml of saturated aqueous ammonium chloride solution and the reaction mixture was then extracted three times with 20 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (24 g cartridge, 35 ml/min, cyclohexane/ethyl acetate gradient). Yield: 320 mg (82% of theory)

後処理

  1. customthe reaction was terminated by addition of 10 ml of saturated aqueous ammonium chloride solution
  2. extractionthe reaction mixture was then extracted three times with 20 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by flash chromatography (24 g cartridge, 35 ml/min, cyclohexane/ethyl acetate gradient)

出典と根拠

ORDレコード
ord-9b294dfd4fb045e29bec3b844a312269
出典データセット
uspto-grants-2016_09
特許番号
US09434690B2

反応ノート

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