Ethyl-12-(m-nitrophenyl)-11-dodecenoate → Ethyl-12-(m-aminophenyl)-dodecanoate

HRID 2226288ノート

反応式

HRID 2226288 の反応式
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1)[CH3:2]

参加物

4

反応物 1

HCID 53714556Ethyl-12-(m-nitrophenyl)-11-dodecenoate

生成物 1

HCID 14584161Ethyl-12-(m-aminophenyl)-dodecanoate収率 97.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

Ethyl-12-(m-nitrophenyl)-11-dodecenoate (9.76 g, 28.1 mmol was dissolved in ethyl acetate (55 ml). The solution was hydrogenated over 5% Pd/C (0.346 g) at room temperature and at an initial pressure of 45 psi for four hours. The reaction mixture was filtered through Celite and the solvent was removed under reduced pressure to yield an oily residue. The crude product was purified by column chromatography (80 g silica gel, hexanes:ethyl acetate, discontinuous gradient 10:1-2:1) to yield the reduced compound 5, ethyl-12-(m-aminophenyl)-dodecanoate (8.75 g, 97.5% yield).

後処理

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was removed under reduced pressure
  3. customto yield an oily residue
  4. customThe crude product was purified by column chromatography (80 g silica gel, hexanes:ethyl acetate, discontinuous gradient 10:1-2:1)

出典と根拠

ORDレコード
ord-fe1c7b133eb34c13ba00377209685fea
出典データセット
uspto-grants-1994_09
特許番号
US05347030

反応ノート

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