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

HRID 1875120노트

반응식

HRID 1875120 반응식
[Li]CCCC.[Cl:6][C:7]1[N:8]=[C:9]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1Cl.CN([CH:33]=[O:34])C>C1COCC1>[Cl:6][C:7]1[N:8]=[C:9]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[CH:33]=[O:34]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 684838634,5-Dichloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazoleHCID 178418339Butyllithium

생성물 1

HCID 715339744-Chloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carbaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

nBuLi (1.3 mL, 2.05 mmol, 1.57 M in hexane) was added dropwise to a solution of 4,5-dichloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole (842 mg, 2.05 mmol) in THF (30 mL) at −78° C. under N2. The mixture was stirred for 30 min and DMF (1.0 mL) was then added dropwise. The mixture was stirred for 20 min and then allowed warm up to room temperature and stirred for 20 min. Quenched by aqueous NH4Cl and extracted with EtOAc and the organic layer was dried over sodium sulfate and concentrated.

후처리

  1. stirringThe mixture was stirred for 20 min
  2. stirringstirred for 20 min
  3. customQuenched by aqueous NH4Cl
  4. extractionextracted with EtOAc
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-429c126995b047d3b45ec5a608c1d3c5
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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