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

HRID 1875120ノート

反応式

HRID 1875120 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-429c126995b047d3b45ec5a608c1d3c5
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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