Sodium hydride → 4-(5-Methyl-3-nitropyrid-2-yl)-4,4-bis(carbethoxy)butyronitrile

HRID 485092

反応式

HRID 485092 の反応式
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH2:11][CH2:12][C:13]#[N:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H-].[Na+].Cl[C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][C:22]([CH3:28])=[CH:21][N:20]=1>O1CCCC1>[CH3:28][C:22]1[CH:23]=[C:24]([N+:25]([O-:27])=[O:26])[C:19]([C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:15])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:11][CH2:12][C:13]#[N:14])=[N:20][CH:21]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 87005Diethyl (2-cyanoethyl)malonateHCID 8183002-Chloro-5-methyl-3-nitropyridine

生成物 1

HCID 202714614-(5-Methyl-3-nitropyrid-2-yl)-4,4-bis(carbethoxy)butyronitrile収率 37.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2-(2-Cyanoethyl)malonic acid diethylester (40 g) was reacted with sodium hydride (4.4 gm) in tetrahydrofuran at 20° C. 2-Chloro-5-methyl-3-nitro-pyridine (35 g) was added and the internal temperature was raised to 100° C. (some tetrahydrofuran distilled off) over 4.25 hrs. The reaction mixture was partitioned between chloroform and water and treated with charcoal. Vacuum distillation of the chloroform extract and then chromatography (CHCl3, silica column) of the distillation residues gave 4-(5-methyl-3-nitropyrid-2-yl)-4,4-bis(carbethoxy)butyronitrile (24.5 g) as a yellow solid m.p. 48°-49° C.

後処理

  1. distillationdistilled off) over 4.25 hrs
  2. customThe reaction mixture was partitioned between chloroform and water
  3. additiontreated with charcoal
  4. distillationVacuum distillation of the chloroform
  5. extractionextract

出典と根拠

ORDレコード
ord-dfb7b561bd274ae5841239121b74ec44
出典データセット
uspto-grants-1985_08
特許番号
US04535163

関連ノート

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