Water → (4-chloro-phenyl)-{4-[hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-1-methyl-1H-pyrrol-2-yl}methanone

HRID 2182818

反応式

HRID 2182818 の反応式
I[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.C([Mg]Br)C.[Cl:30][C:31]1[CH:46]=[CH:45][C:34]([C:35]([C:37]2[N:41]([CH3:42])[CH:40]=[C:39]([CH:43]=[O:44])[CH:38]=2)=[O:36])=[CH:33][CH:32]=1.O>C(Cl)Cl.CCOCC>[Cl:30][C:31]1[CH:46]=[CH:45][C:34]([C:35]([C:37]2[N:41]([CH3:42])[CH:40]=[C:39]([CH:43]([OH:44])[C:2]3[N:3]=[CH:4][N:5]([C:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:6]=3)[CH:38]=2)=[O:36])=[CH:33][CH:32]=1

参加物

7

反応物 4

HCID 962WaterHCID 6182524-Iodo-1-tritylimidazoleHCID 224810525-(4-Chlorobenzoyl)-1-methyl-1H-pyrrole-3-carboxaldehydeHCID 178418443HCID 178418443、化合物

生成物 1

HCID 22481044(4-chloro-phenyl)-{4-[hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-1-methyl-1H-pyrrol-2-yl}methanone収率 138.9%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To 4.4 g (0.01 mole) 4-iodo-1-tritylimidazole in 80 mL of CH2Cl2 was added dropwise 3.3 mL of 3.0 M ethylmagnesium bromide in Et2O. After stirring for 1 h, a solution of 1.0 g (0.004 mole) of 5-(4-chlorobenzoyl)-1-methyl-1H-pyrrole-3-carboxaldehyde in 10 mL of CH2Cl2 was added dropwise. The resulting reaction mixture was stirred for 2.5 h after which it was poured into water. The solid was filtered off through celite. The organics from the filtrate were separated off, washed with water, brine and dried (Na2SO4). The solvent was evaporated in vacuo to give 3.1 g of (4-chlorophenyl)-{4-[hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-1-methyl-1H-pyrrol-2yl}-methanone: CI-MS m/z=559 (M++H). 1HNMR (CDCl3) δ 7.7 (m, 5H) 7.4-7.0 (m, 16H); 6.5 (m, 1H); 3.75 (s, 3H).

後処理

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 2.5 h after which it
  3. filtrationThe solid was filtered off through celite
  4. customThe organics from the filtrate were separated off
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated in vacuo

出典と根拠

ORDレコード
ord-2d04f7b6ce2b4a2baea1c6d9975d5c5f
出典データセット
uspto-grants-2005_05
特許番号
US06897319B2

関連ノート

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