Water → HCID 11091612、化合物

HRID 433594ノート

反応式

HRID 433594 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 11091612HCID 11091612、化合物収率 66.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-8d1d0cd631a8473e8877eaa9171b52ae
出典データセット
uspto-grants-2003_12
特許番号
US06667335B2

反応ノート

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