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

HRID 1875119노트

반응식

HRID 1875119 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-cedab6d9959d4b52ab73d2a341917eca
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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