4-Dimethylamino-1-naphthaldehyde → (4-(dimethylamino)naphthalen-1-yl)(4-methyl-1-trityl-1H-imidazol-5-yl)methanol

HRID 907512ノート

反応式

HRID 907512 の反応式
[CH3:1][C:2]1[N:6]([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:5]=[N:4][C:3]=1[CH2:26][OH:27].I[C:29]1[N:30]([C:35]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:31]=[C:32]([CH3:34])[N:33]=1.C([Mg]Br)C.[CH3:58][N:59]([CH3:72])[C:60]1[C:69]2[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=2)[C:63]([CH:70]=[O:71])=[CH:62][CH:61]=1>ClCCl.CO>[CH3:31][N:30]([CH3:29])[C:35]1[C:42]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:52]([CH:26]([C:3]2[N:4]=[CH:5][N:6]([C:7]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:2]=2[CH3:1])[OH:27])=[CH:53][CH:48]=1.[CH3:58][N:59]([CH3:72])[C:60]1[C:69]2[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=2)[C:63]([CH:70]([C:31]2[N:30]([C:35]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:29]=[N:33][C:32]=2[CH3:34])[OH:71])=[CH:62][CH:61]=1

参加物

8

反応物 4

HCID 6080524-Dimethylamino-1-naphthaldehydeHCID 10411451iodo-4-methyl-1-trityl-1H-imidazoleHCID 11544901(5-Methyl-1-trityl-1H-imidazol-4-yl)methanolHCID 178418443HCID 178418443、化合物

生成物 2

HCID 67026323(4-(dimethylamino)naphthalen-1-yl)(5-methyl-1-trityl-1H-imidazol-4-yl)methanolHCID 67026330(4-(dimethylamino)naphthalen-1-yl)(4-methyl-1-trityl-1H-imidazol-5-yl)methanol収率 87%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

(4-Dimethylamino)naphthalen-1-yl)(5-methyl-1-trityl-1H-imidazol-4-yl)methanol and (4-(dimethylamino)naphthalen-1-yl)-4-methyl-1-trityl-1H-imidazol-5-yl)methanol (4): A solution of (2) (5.1 g, 11.3 mmol) in dichloromethane (70 ml) was added ethyl magnesium bromide (3.0 M in diethyl ether, 3.8 mL, 11.4 mmol) drop wise at rt. The mixture was stirred for 1 h and a solution of 4-(dimethylamino)-1-naphthaldehyde (3) (1.15 g, 7.35 mmol) in dichloromethane (30 mL) was added drop wise via addition funnel. The reaction mixture was stirred at room temperature (n) overnight. The reaction mixture was quenched with ammonium chloride (aq). The resulting aqueous layer was extracted twice with dichloromethane (300 mL). The pooled organic layers were dried over magnesium sulfate. The mixture was filtered, and the solvents were removed under vacuum. The residue was purified by chromatography on silica gel with 1 to 2% saturated ammonia methanol in dichloromethane to give a crude (4-(dimethylamino)naphthalen-1-yl)(5-methyl-1-trityl-1H-imidazol-4-yl)methanol and (4-(dimethylamino)naphthalen-1-yl)(4-methyl-1-trityl-1H-imidazol-5-yl)methanol (4) (3.35 g, 6.40 mmol, 87% yield).

後処理

  1. additionwise via addition funnel
  2. customThe reaction mixture was quenched with ammonium chloride (aq)
  3. extractionThe resulting aqueous layer was extracted twice with dichloromethane (300 mL)
  4. dry with materialThe pooled organic layers were dried over magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customthe solvents were removed under vacuum
  7. customThe residue was purified by chromatography on silica gel with 1 to 2% saturated ammonia methanol in dichloromethane

出典と根拠

ORDレコード
ord-35d00d6e4f724ae586fa2ce64b25fbf8
出典データセット
uspto-grants-2011_09
特許番号
US08013169B2

反応ノート

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