Acetonitrile → 5-(tert-butyldiphenylsilyloxymethyl)-4-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazole

HRID 2273306

反応式

HRID 2273306 の反応式
[Si:1]([O:18][CH2:19][C:20]1[N:21]=[CH:22][N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][Si:34]([CH3:41])([CH3:40])[CH2:35][CH2:36][O:37][CH2:38]Cl.[C:42](#N)C>>[Si:1]([O:18][CH2:19][C:20]1[N:21]=[CH:22][N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:24]=1[CH3:33])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1.[Si:1]([O:18][CH2:19][C:20]1[N:21]([CH2:38][O:37][CH2:36][CH2:35][Si:34]([CH3:41])([CH3:40])[CH3:33])[CH:22]=[N:23][C:24]=1[CH3:42])([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 710872934-(tert-Butyldiphenylsilyloxymethyl)-1-(2-trimethylsilylethoxy methyl)-1H-imidazole

生成物 2

HCID 710871795-(tert-butyldiphenylsilyloxymethyl)-4-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazoleHCID 710874044-(tert-butyldiphenylsilyloxymethyl)-5-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazole

実験手順

The mixture obtained in (1) (35.4 g) was dissolved in acetonitrile (500 mL), TEA (37.8 mL) and then 2-trimethylsilylethoxymethyl chloride (21.4 mL) were added under ice cooling and stirring, and stirring was conducted at 70° C. for 12 hours. The reaction mixture was allowed to cool to room temperature, and the solvent was distilled off under reduced pressure. The residue was diluted with ethyl acetate, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by flash chromatography (ethyl acetate/hexane=15%→50%) using a silica gel column (trade name: Cartridge 65i, manufactured by Biotage Ltd.) to give 4-(tert-butyldiphenylsilyloxymethyl)-5-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazole (17.9 g) as a low polarity component and 5-(tert-butyldiphenylsilyloxymethyl)-4-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazole (9.42 g) as a high polarity component.

後処理

  1. stirringstirring
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by flash chromatography (ethyl acetate/hexane=15%→50%)

出典と根拠

ORDレコード
ord-0d44d193e92f4ecd92805debf3c3936a
出典データセット
uspto-grants-2015_09
特許番号
US09120835B2

関連ノート

読み込み中…