Imidazole → 4,5-Dichloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole

HRID 1875119ノート

反応式

HRID 1875119 の反応式
N1C=CN=C1.[Cl:6][C:7]1[N:8]=[C:9]([CH2:21][OH:22])[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[Cl:12].Cl[Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].[NH4+].[Cl-]>C(Cl)Cl>[Cl:6][C:7]1[N:8]=[C:9]([CH2:21][O:22][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[C:11]=1[Cl:12]

参加物

6

反応物 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 68487065[4,5-Dichloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazol-2-yl]methanol

生成物 1

HCID 684838634,5-Dichloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole収率 99.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Imidazole (282 mg, 4.14 mmol) was added to a solution of [4,5-dichloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazol-2-yl]methanol (614 mg, 2.07 mmol) and chloro(1,1-dimethylethyl)dimethylsilane (345 mg, 2.28 mmol) in DCM (8 mL) at RT under N2. The mixture was stirred overnight. Aqueous NH4Cl was then added. Extracted with DMC and the extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography (0-10% EtOAc in hexane) to give the title compound (845 mg, 99%) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.42 (2H, s) 4.74 (2H, s) 3.53-3.59 (2H, m) 0.87-0.95 (11H, m) 0.09 (6H, s) 0.00 (9H, s). LCMS: m/z 411 (M+1).

後処理

  1. extractionExtracted with DMC
  2. dry with materialthe extracts were dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (0-10% EtOAc in hexane)

出典と根拠

ORDレコード
ord-cedab6d9959d4b52ab73d2a341917eca
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

読み込み中…