Chlorotriethylsilane → 1-Ethoxymethyl-4-(triethylsilyloxymethyl)-1H-imidazole

HRID 242370ノート

反応式

HRID 242370 の反応式
[CH2:1]([O:3][CH2:4][N:5]1[CH:9]=[C:8]([CH2:10][OH:11])[N:7]=[CH:6]1)[CH3:2].[CH2:12]([Si:14](Cl)([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:13]>ClCCl.CN(C1C=CN=CC=1)C.O>[CH2:1]([O:3][CH2:4][N:5]1[CH:9]=[C:8]([CH2:10][O:11][Si:14]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:12][CH3:13])[N:7]=[CH:6]1)[CH3:2]

参加物

6

反応物 2

HCID 13819ChlorotriethylsilaneHCID 682713641-Ethoxymethyl-1H-imidazole-4-methanol

生成物 1

HCID 710871261-Ethoxymethyl-4-(triethylsilyloxymethyl)-1H-imidazole

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

The compound (520 mg) obtained in (2) was dissolved in dichloromethane (30 mL), followed by addition of triethylsilyl chloride (1.12 mL), TEA (1.16 mL) and DMAP (catalytic amount) under stirring, and the stirring was continued for 17 hours. The reaction solution was diluted with water, and extracted with chloroform. The combined extract was washed with saturated brine, dried over anhydrous sodium sulfate, and subsequently the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=10%→80%) using silica gel column (product name: SNAP Cartridge KP-Sil 50 g, manufactured by Biotage, Ltd.) to afford the title compound (665 mg).

後処理

  1. extractionextracted with chloroform
  2. extractionThe combined extract
  3. washwas washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationsubsequently the solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=10%→80%)

出典と根拠

ORDレコード
ord-cb1d220ce0b448339ed7b40c8f9dd220
出典データセット
uspto-grants-2014_02
特許番号
US08653126B2

反応ノート

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