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Sodium hydride → 3-[({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]methyl}oxy)methyl]benzonitrile

HRID 606467
ノート
印刷プレビュー

反応式

HRID 606467 の反応式
[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH:12]=[N:11][C:10]([CH2:13][OH:14])=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[C:32]#[N:33].[H-].[Na+]>C1COCC1>[C:21]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:8]2[CH:12]=[N:11][C:10]([CH2:13][O:14][CH2:28][C:29]3[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=3)[C:32]#[N:33])=[N:9]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 13471694(1-trityl-1H-1,2,4-triazol-3-yl)methanol

生成物 1

HCID 667690183-[({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]methyl}oxy)methyl]benzonitrile収率 87%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

A suspension of [1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]methanol obtained in Reference Example 36 (3.00 g, 8.79 mmol), 3-(bromomethyl)benzonitrile (1.89 g, 9.67 mmol) and 60% sodium hydride (oil dispersion, 0.316 g, 13.2 mmol) in THF (100 mL) was stirred at 70° C. for 15 hr. The reaction mixture was cooled to room temperature, and extracted with water and ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (10-30% ethyl acetate/hexane) to give the title compound as a colorless oil (3.50 g, 87%).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with water and ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (10-30% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-0c3e3a2fbce9499bbea021a0575ccbc5
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07915267B2

反応ノート

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