Tetrahydrofuran → 1-(4-Nitrobenzyl)-2-butyl-4-chloro-5-(2-phenylethen-1-yl)imidazole

HRID 465843

反応式

HRID 465843 の反応式
[Li][CH2:2][CH2:3][CH2:4][CH3:5].[N+:6]([C:9]1[CH:27]=[CH:26][C:12]([CH2:13][N:14]2[C:18]([CH:19]=O)=[C:17]([Cl:21])[N:16]=[C:15]2[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:11][CH:10]=1)([O-:8])=[O:7].[CH2:28]1[CH2:32]OC[CH2:29]1>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1>[N+:6]([C:9]1[CH:27]=[CH:26][C:12]([CH2:13][N:14]2[C:18]([CH:19]=[CH:5][C:4]3[CH:32]=[CH:28][CH:29]=[CH:2][CH:3]=3)=[C:17]([Cl:21])[N:16]=[C:15]2[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:11][CH:10]=1)([O-:8])=[O:7]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 198153972-Butyl-5-chloro-3-(4-nitro-benzyl)-3h-imidazole-4-carbaldehydeHCID 178418339Butyllithium2 回

生成物 1

HCID 541136611-(4-Nitrobenzyl)-2-butyl-4-chloro-5-(2-phenylethen-1-yl)imidazole

試薬・触媒・溶媒 1

HCID 70671Benzyltriphenylphosphonium chloride触媒

実験手順

A solution of 0.4 g of benzyltriphenylphosphonium chloride in 20 mL of dried THF was cooled to -30°. To the above solution was added 0.65 mL of 1.6M n-BuLi dropwise. As the BuLi was added the solution turned to deep orange color. After stirring for 10 min. at -30°, 0.32 g of 1-(4-nitrobenzyl)-2-butyl-4-chloroimidazole-5-aldehyde was added and the reaction mixture was allowed to warm up to room temperature and stirred at room temperature for 2 hours. The reaction mixture was quenched with 2 mL of saturated NH4Cl solution and diluted with ethyl acetate, and the ethyl acetate solution was washed with water and a brine solution. Evaporation gave a thick oily residue which was purified by the flash silica gel column chromatography (hexane:ethyl acetate=3:1 elution) to give a thick yellow oil, 0.39 g.

後処理

  1. stirringstirred at room temperature for 2 hours
  2. customThe reaction mixture was quenched with 2 mL of saturated NH4Cl solution
  3. additiondiluted with ethyl acetate
  4. washthe ethyl acetate solution was washed with water
  5. customEvaporation
  6. customgave a thick oily residue which
  7. customwas purified by the flash silica gel column chromatography (hexane:ethyl acetate=3:1 elution)
  8. customto give a thick yellow oil, 0.39 g

出典と根拠

ORDレコード
ord-5bcb189e96c045daaa4ad2635e3231a2
出典データセット
uspto-grants-1992_10
特許番号
US05153197

関連ノート

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