Dimethylformamide → methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate

HRID 1409425노트

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HRID 1409425 반응식
Br[C:2]1[N:3]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.C([Mg]Cl)(C)C.CN([CH:27]=[O:28])C>C1COCC1>[CH:27]([C:2]1[N:3]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1)=[O:28]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 58638548Methyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylateHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 58638526methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-40 °C

실험 절차

Into a flask containing methyl 2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate (5 g, 14.9 mmol) in THF (20 ml), 2 M solution of i-PrMgCl in THF (22.4 ml, 44.9 mmol) was added at −40° C. under nitrogen atmosphere. The resulting mixture was allowed to stir for 10 min at −40° C. and cooled to −78° C. The reaction mixture was treated with DMF (7.29 ml, 89.8 mmol) and slowly warmed to RT. The mixture was stirred for 1 h at RT and quenched with saturated aqueous solution of NaHCO3. The crude was extracted with EtOAc. The organic layer was concentrated under reduced pressure. Yield 3 g. LC-MS: [M+1]=285.15.

후처리

  1. additionwas added at −40° C. under nitrogen atmosphere
  2. temperaturecooled to −78° C
  3. temperatureslowly warmed to RT
  4. stirringThe mixture was stirred for 1 h at RT
  5. customquenched with saturated aqueous solution of NaHCO3
  6. extractionThe crude was extracted with EtOAc
  7. concentrationThe organic layer was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c3cd757b25864047a5361c11220083db
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921378B2

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