Ethyl cyanoformate → Ethyl 4-cyano-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-imidazole-2-carboxylate

HRID 32920

반응식

HRID 32920 반응식
Br[C:2]1[N:3]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:4]=[C:5]([C:7]#[N:8])[N:6]=1.C([Mg]Cl)(C)C.C([C:24]([O:26][CH2:27][CH3:28])=[O:25])#N>C1COCC1>[CH2:27]([O:26][C:24]([C:2]1[N:3]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:4]=[C:5]([C:7]#[N:8])[N:6]=1)=[O:25])[CH3:28]

참가 물질

5

반응물 3

HCID 69336Ethyl cyanoformateHCID 579205782-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carbonitrileHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 67188254Ethyl 4-cyano-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-imidazole-2-carboxylate수율 75.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

To a solution of 2-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile (0.55 g, 1.8 mmol) (as prepared in the previous step) in THF (6 mL) at −40° C. was added dropwise a solution of 2M i-PrMgCl in THF (1 mL). The reaction was allowed to stir for 10 min at −40° C. and then cooled to −78° C., and ethyl cyanoformate (0.3 g, 3.0 mmol) was added. The reaction allowed to attain RT and stirred for 1 h. The reaction was quenched with satd aq NH4Cl, diluted with EtOAc (20 mL) and washed with brine (2×20 mL), and the organic layer was dried over Na2SO4 and then concentrated. The title compound was eluted from a 20-g SPE cartridge (silica) with 30% EtOAc/hexane to give 0.40 g (74%) of a colorless oil. Mass spectrum (ESI, m/z): Calcd. for C13H21N3O3Si, 296.1 (M+H), found 296.1.

후처리

  1. temperaturecooled to −78° C.
  2. customto attain RT
  3. stirringstirred for 1 h
  4. customThe reaction was quenched with satd aq NH4Cl
  5. additiondiluted with EtOAc (20 mL)
  6. washwashed with brine (2×20 mL)
  7. dry with materialthe organic layer was dried over Na2SO4
  8. concentrationconcentrated
  9. washThe title compound was eluted from a 20-g SPE cartridge (silica) with 30% EtOAc/hexane

출처 및 근거

ORD 기록
ord-6174ef22ddd04e3fb1dba4dc7efa5329
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427683B2

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