2-Methyl-5-nitro-2-pentene → Methyl 3,7-dimethyl-4-nitro-6-octenoate

HRID 1447531

反応式

HRID 1447531 の反応式
CC12CCCCN1C=CCNC2.[CH3:13][C:14](=[CH:16][CH2:17][CH2:18][N+:19]([O-:21])=[O:20])[CH3:15].[C:22]([O:27][CH3:28])(=[O:26])/[CH:23]=[CH:24]/[CH3:25]>CO>[CH3:25][CH:24]([CH:18]([N+:19]([O-:21])=[O:20])[CH2:17][CH:16]=[C:14]([CH3:15])[CH3:13])[CH2:23][C:22]([O:27][CH3:28])=[O:26]

参加物

5

反応物 3

HCID 5346332-Methyl-5-nitro-2-penteneHCID 638132Methyl CrotonateHCID 20384084HCID 20384084、化合物

生成物 1

HCID 23341447Methyl 3,7-dimethyl-4-nitro-6-octenoate収率 42%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

Methyl 3,7-Diazabicyclo[5,4,0]undec-5-ene (4 ml) is added to a solution of 2-methyl-5-nitro-2-pentene (25.0 g, 0.193 m) in methanol (200 ml). The resulting mixture is heated to 60° and methyl crotonate (30.85 g, 0.308 m) is added under nitrogen. The mixture is then stirred for 6 days at 60° after which it is cooled to room temperature and most of the methanol is removed in vacuo. The residue is treated with ether (500 ml) and washed with 2 N HCl (250 ml) and water (250 ml). The organic layer is dried (Na2SO4) and evaporated in vacuo to give 42.5 g of crude product. The crude product is purified by column chromatography on silica gel (500 g, ethyl acetate/hexane 2:98) to give methyl 3,7-dimethyl-4-nitro-6-octenoate (8.65 g, 42%).

後処理

  1. temperatureThe resulting mixture is heated to 60°
  2. customis removed in vacuo
  3. additionThe residue is treated with ether (500 ml)
  4. washwashed with 2 N HCl (250 ml) and water (250 ml)
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. customevaporated in vacuo
  7. customto give 42.5 g of crude product
  8. customThe crude product is purified by column chromatography on silica gel (500 g, ethyl acetate/hexane 2:98)

出典と根拠

ORDレコード
ord-a5c2699945e04fde97f7c56979c22d81
出典データセット
uspto-grants-1979_12
特許番号
US04177194

関連ノート

読み込み中…