Nitromethane → Ethyl 3-(4-chlorophenyl)-4-nitrobutanoate

HRID 1402839

反応式

HRID 1402839 の反応式
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.CN(C)C(N(C)C)=N.[N+:23]([CH3:26])([O-:25])=[O:24]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([CH2:26][N+:23]([O-:25])=[O:24])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=1

参加物

4

反応物 3

HCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 2014712-Propenoic acid, 3-(4-chlorophenyl)-, ethyl ester

生成物 1

HCID 11097654Ethyl 3-(4-chlorophenyl)-4-nitrobutanoate収率 92.9%

実験手順

The solution of ethyl 4-chlorocinnamate (12.6 g) and N,N,N′,N′-tetramethylguanidine (1.2 g) in nitromethane (36.6 g) was kept at rt for three days. The excess of nitromethane was evaporated and the residue dissolved in diethyl ether (250 ml). The organic layer was washed with 2M HCl (2×150 ml), dried (sodium sulfate), and evaporated. The residue was subjected to purification by flash chromatography on silica gel (petrol ether/ethyl acetate 10:1) to give ethyl 3-(4-chlorophenyl)-4-nitrobutanoate (15.1 g) as yellowish oil.

後処理

  1. customThe excess of nitromethane was evaporated
  2. dissolutionthe residue dissolved in diethyl ether (250 ml)
  3. washThe organic layer was washed with 2M HCl (2×150 ml)
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. customThe residue was subjected to purification by flash chromatography on silica gel (petrol ether/ethyl acetate 10:1)

出典と根拠

ORDレコード
ord-5c511d6b0d524f17a4214faf2eba502b
出典データセット
uspto-grants-2014_12
特許番号
US08912186B2

関連ノート

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