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Acetone → 2-(1-{5-[2-(Tert-butyldimethylsilanyloxy)-ethyl]-imidazol-1-yl}-2-hydroxy-2-methyl-propyl)-benzonitrile

HRID 1690749
ノート
印刷プレビュー

反応式

HRID 1690749 の反応式
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[N:15]([CH2:16][C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[C:19]#[N:20])[CH:14]=[N:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:35][C:36]([CH3:38])=[O:37]>C1COCC1>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[N:15]([CH:16]([C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[C:19]#[N:20])[C:36]([OH:37])([CH3:38])[CH3:35])[CH:14]=[N:13][CH:12]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]
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 180AcetoneHCID 2733832Lithium hexamethyldisilazaneHCID 57781102HCID 57781102、化合物

生成物 1

HCID 577810882-(1-{5-[2-(Tert-butyldimethylsilanyloxy)-ethyl]-imidazol-1-yl}-2-hydroxy-2-methyl-propyl)-benzonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

2-{5-[2-(tert-Butyldimethylsilanyloxy)-ethyl]-imidazol-1-ylmethyl}-benzonitrile (1.14 g, 3.34 mmol) is dissolved in THF (20 mL) and cooled to −78° C. LHMDS (1M in THF, 5 mL, 5 mmol) is added dropwise. Ten min after the end of addition, acetone (0.295 g, 5.01 mmol) is added. The reaction mixture is stirred at −78° C. for 40 min. It is then quenched with saturated aqueous sodium bicarbonate (10 mL). The mixture is allowed to warm to room temperature, then poured into water. After extraction with ethyl acetate the organic phase is dried over Na2SO4 and concentrated in vacuo to give 2-(1-{5-[2-(tert-butyldimethylsilanyloxy)-ethyl]-imidazol-1-yl}-2-hydroxy-2-methyl-propyl)-benzonitrile; MS (ESI) m/z 400.3 (M+H)

後処理

  1. additionis added
  2. customIt is then quenched with saturated aqueous sodium bicarbonate (10 mL)
  3. temperatureto warm to room temperature
  4. additionpoured into water
  5. extractionAfter extraction with ethyl acetate the organic phase
  6. dry with materialis dried over Na2SO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8475d40bbd5f46ce8da91fe6814838c2
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08153674B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート