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2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-acrylic acid ethyl ester → 2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-propionic acid ethyl ester

HRID 2101500
ノート
印刷プレビュー

反応式

HRID 2101500 の反応式
[CH2:1]([O:3][C:4](=[O:28])[C:5]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:6][C:7]1[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)[CH:9]=[CH:10][N:11]=1)[CH3:2]>C(O)C.[Ni].O>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:6][C:7]1[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)[CH:9]=[CH:10][N:11]=1)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 1

HCID 688632652-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-acrylic acid ethyl ester

生成物 1

HCID 119553452-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-propionic acid ethyl ester収率 94%

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of 2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-acrylic acid ethyl ester, (409 mg, 0.99 mmol) in absolute ethanol (30 mL) was added Raney nickel active catalyst (approximately 1 g of a 50% suspension in water). The reaction flask was flushed with N2 prior to flushing with H2 via a balloon. The reaction was stirred at ambient temperature for 14 h under a balloon atmosphere of H2. After flushing with N2, the reaction was filtered through a plug of celite and the filtrate concentrated in vacuo. The resulting residue was partitioned with CH2Cl2 (10 mL) and saturated NaHCO3 (5 mL). The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo to afford 2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-propionic acid ethyl ester (385 mg, 94%) as a colorless oil: ESI MS m/z 417 [C22H22Cl2N2O2+H]+.

後処理

  1. customThe reaction flask was flushed with N2
  2. customto flushing with H2 via a balloon
  3. customAfter flushing with N2
  4. filtrationthe reaction was filtered through a plug of celite
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe resulting residue was partitioned with CH2Cl2 (10 mL) and saturated NaHCO3 (5 mL)
  7. washThe organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f841fe2ba5724e2ba0e30990a5541df5
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07572921B2

反応ノート

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