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Imidazole → 5-(Tert-butyldimethylsilanyloxymethyl)-pyridine-2-carbonitrile

HRID 76354
ノート
印刷プレビュー

反応式

HRID 76354 の反応式
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1.[C:11]([Si:15]([CH3:18])([CH3:17])Cl)([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1.O>CN(C)C=O>[Si:15]([O:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:18])[CH3:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 122519662-Cyano-5-hydroxymethylpyridine

生成物 1

HCID 542127655-(Tert-butyldimethylsilanyloxymethyl)-pyridine-2-carbonitrile収率 84.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

実験手順

5-(Hydroxymethyl)pyridine-2-carbonitrile (258 mg) was dissolved in dimethylformamide (8 ml), tert-butyl dimethylchlorosilane (347 mg) and imidazole (326 mg) were added, and the mixture was stirred at room temperature for 1% hr. Water (20 ml) was added and the mixture was stirred, extracted with ethyl acetate (once with 50 ml and once with 20 ml), washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 2 L, elution solvent: hexane/ethyl acetate) to give the title compound (405 mg).

後処理

  1. stirringthe mixture was stirred
  2. extractionextracted with ethyl acetate (once with 50 ml
  3. washonce with 20 ml), washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 2 L, elution solvent: hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-fa370009765446999623399fc31b82e4
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08835631B2

反応ノート

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