Hexane → Ethyl 2-methyl-1-(2-(trimethylsilyl)ethoxymethyl)-1H-thieno[2,3-d]imidazol-5-carboxlate

HRID 1072802ノート

反応式

HRID 1072802 の反応式
CC[O-].[Na+].[C:5]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:6][SH:7].Br[C:13]1[N:14]=[C:15]([CH3:28])[N:16]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:17]=1[CH:18]=O.CCCCCC>C(O)C>[CH3:28][C:15]1[N:16]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:26])([CH3:25])[CH3:27])[C:17]2[CH:18]=[C:6]([C:5]([O:9][CH2:10][CH3:11])=[O:8])[S:7][C:13]=2[N:14]=1

参加物

6

反応物 4

HCID 8058HexaneHCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxideHCID 220586064-Bromo-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)imidazole-5-carbaldehyde

生成物 1

HCID 22387741Ethyl 2-methyl-1-(2-(trimethylsilyl)ethoxymethyl)-1H-thieno[2,3-d]imidazol-5-carboxlate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒3 回

反応条件

温度
80 °C

実験手順

2.68 M Sodium ethylate was dissolved in ethanol (50 ml) and a solution (25 ml) of ethyl thioglycolate in ethanol was added. Thereto was added a solution (150 ml) of 4-bromo-2-methyl-1-(2-(trimethylsilyl)ethoxymethyl)imidazol-5-carboxaldehyde (3.16 g) in ethanol and the mixture was stirred at 80° C. for 2 hr. The solvent was evaporated under reduced pressure and water was added. The mixture was extracted twice with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was obtained by silica gel column chromatography (hexane/ethyl acetate=9/1). Hexane was added to the purified product and crystals were collected by filtration to give the objective compound (765 mg) as pale-brown crystals.

後処理

  1. customThe solvent was evaporated under reduced pressure and water
  2. additionwas added
  3. extractionThe mixture was extracted twice with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was obtained by silica gel column chromatography (hexane/ethyl acetate=9/1)
  8. filtrationwere collected by filtration

出典と根拠

ORDレコード
ord-49ad1330475041a9a3366b77c0552228
出典データセット
uspto-grants-2005_06
特許番号
US06911469B2

反応ノート

読み込み中…