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

HRID 251747노트

반응식

HRID 251747 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-783a28ba87394c4e8e20f7cfec405ea3
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863294B2

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