Water → HCID 11091612, 화합물

HRID 397900노트

반응식

HRID 397900 반응식
[I:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[I:7].[H-].[Na+].[CH3:10][Si:11]([CH3:18])([CH3:17])[CH2:12][CH2:13][O:14][CH2:15]Cl.O>CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[N:3]=[CH:4][N:5]([CH2:15][O:14][CH2:13][CH2:12][Si:11]([CH3:18])([CH3:17])[CH3:10])[C:6]=1[I:7]

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 27733824,5-Diiodo-1H-imidazole

생성물 1

HCID 11091612HCID 11091612, 화합물수율 66.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

4,5-Diiodoimidazole (prepared according to D. S. Carver, S. D. Lindell, and E. A. Saville-Stones, Tetrahedron, 1997, 53, 42, 14481-14496) (10.1 g, 31.6 mmol) was added portionwise to a room temperature suspension of sodium hydride (1.38 g, 31.6 mmol, 55% *in mineral oil) in dry DMF (45 ml). The reaction mixture was stirred at room temperature for 90 min, then cooled to 0° C. and treated slowly with a solution of 2-(trimethylsilyl)-ethoxymethylchloride (6.81 ml, 34.7 mmol) in DMF (10 ml). After 2 h stirring at 0° C., the reaction mixture was poured onto a mixture of H2O (200 ml) and AcOEt (50 ml). The mixture was filtered and the mother liquor was extracted 3 times with AcOEt. The combined extracts were dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was chromatographed (silica, elution with hexane/AcOEt=9:1) to provide the title compound (9.44 g, 66.4%) as a pale yellow oil. MS: m/e=450.0 (M+).

후처리

  1. additionSaville-Stones, Tetrahedron, 1997, 53, 42, 14481-14496) (10.1 g, 31.6 mmol) was added portionwise to a room temperature
  2. temperaturecooled to 0° C.
  3. stirringAfter 2 h stirring at 0° C.
  4. filtrationThe mixture was filtered
  5. extractionthe mother liquor was extracted 3 times with AcOEt
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customThe residue was chromatographed
  10. wash(silica, elution with hexane/AcOEt=9:1)

출처 및 근거

ORD 기록
ord-54d128c8604044aeb90ec071eeedb82a
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610723B2

반응 노트

불러오는 중…