Imidazole → Trans-1-{6-[alpha-(4-chlorophenyl)-2,4-dichlorobenzyloxy]tetrahydropyran-2-ylmethyl}imidazole

HRID 905063

反応式

HRID 905063 の反応式
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([O:24][C@@H:25]2[O:30][C@@H:29]([CH2:31]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:28][CH2:27][CH2:26]2)[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:11][CH:10]=1.[I-].[Na+]>CN(C)C=O.O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([O:24][C@@H:25]2[O:30][C@@H:29]([CH2:31][N:3]3[CH:7]=[CH:6][N:5]=[CH:4]3)[CH2:28][CH2:27][CH2:26]2)[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:13][CH:14]=1

参加物

7

反応物 4

HCID 795ImidazoleHCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 53867744Trans-6-[alpha-(4-chlorophenyl)-2,4-dichlorobenzyloxy]-2-tosyloxymethyltetrahydropyran

生成物 1

HCID 13073922Trans-1-{6-[alpha-(4-chlorophenyl)-2,4-dichlorobenzyloxy]tetrahydropyran-2-ylmethyl}imidazole収率 75.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

114 mg of 55% sodium hydride were added to a solution of 323 mg of imidazole in 10 ml of dimethylformamide, and, after the mixture had been stirred at 80° C. for 30 minutes, it was cooled to room temperature. There were then added 2.20 g of trans-6-[α-(4-chlorophenyl)-2,4-dichlorobenzyloxy]-2-tosyloxymethyltetrahydropyran, dissolved in 15 ml of dimethylformamide, and then 594 mg of sodium iodide were added to the mixture. The resulting mixture stirred under a stream of nitrogen at 90°-95° C. for 4 hours, after which it was cooled, diluted with water and extracted with diethyl ether. The ethereal extract was washed with water and dried over sodium sulphate, after which it was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography through silica gel eluted with a 8:1:0.1 by volume mixture of ethyl acetate, benzene and triethylamine, to give 1.346 g of the title compound as a colourless oil.

後処理

  1. temperatureit was cooled to room temperature
  2. stirringThe resulting mixture stirred under a stream of nitrogen at 90°-95° C. for 4 hours
  3. temperatureafter which it was cooled
  4. extractionextracted with diethyl ether
  5. extractionThe ethereal extract
  6. washwas washed with water
  7. dry with materialdried over sodium sulphate
  8. concentrationafter which it was concentrated by evaporation under reduced pressure
  9. customthe residue was purified by column chromatography through silica gel
  10. washeluted with a 8:1:0.1 by volume mixture of ethyl acetate, benzene and triethylamine

出典と根拠

ORDレコード
ord-480fb030c2094e639f142434abd29276
出典データセット
uspto-grants-1983_12
特許番号
US04421758

関連ノート

読み込み中…