Dimethylformamide → 4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole-2-carbaldehyde

HRID 251747ノート

反応式

HRID 251747 の反応式
[Si:1]([O:8][CH2:9][C:10]1[N:11]=[CH:12][N:13]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li]CCCC.CN([CH:31]=[O:32])C>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[N:11]=[C:12]([CH:31]=[O:32])[N:13]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:21])[CH3:22])[CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 220223854-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazoleHCID 178418339Butyllithium

生成物 1

HCID 575803574-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole-2-carbaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

To a stirred solution of 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole (See WO03/022274) (1 eq) in THF at 40° C. was added dropwise a solution of BuLi (2 eq.) in hexanes and the mixture was stirred at 40° C. for a further 30 min. DMF (4 eq.) was then added and the cooling bath was removed and the reaction mixture was allowed to warm to RT and stirred for 30 min, after which time it was quenched by addition of a sat. aq. NH4Cl solution. The organics were extracted with EtOAc (2×), washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The material was purified by column chromatography on silica eluting with 15% EtOAc/petroleum ether. 1H NMR (300 MHz, CDCl3) δ: 9.81 (1H, s), 7.30 (1H, s), 5.95 (2H, s), 4.87, (2H, s), 3.58 (2H, t, J=7.7 Hz), 1.05-0.85 (20H, m), 0.05 (6H, s).

後処理

  1. customat 40° C.
  2. customthe cooling bath was removed
  3. temperatureto warm to RT
  4. stirringstirred for 30 min
  5. customafter which time it was quenched by addition of a sat. aq. NH4Cl solution
  6. extractionThe organics were extracted with EtOAc (2×)
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure
  10. customThe material was purified by column chromatography on silica eluting with 15% EtOAc/petroleum ether

出典と根拠

ORDレコード
ord-783a28ba87394c4e8e20f7cfec405ea3
出典データセット
uspto-grants-2011_01
特許番号
US07863294B2

反応ノート

読み込み中…