Imidazole → 1-(tert-Butyldiphenylsilyloxy)propyl iodide

HRID 231603

反応式

HRID 231603 の反応式
[I:1][CH2:2][CH2:3][CH2:4]O.N1C=CN=C1.[C:11]([Si:15](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:14])([CH3:13])[CH3:12].[OH2:29]>CN(C)C=O>[Si:15]([O:29][CH:2]([I:1])[CH2:3][CH3:4])([C:11]([CH3:14])([CH3:13])[CH3:12])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 693903-Iodo-1-propanolHCID 94078tert-Butyldiphenylchlorosilane

生成物 1

HCID 198228821-(tert-Butyldiphenylsilyloxy)propyl iodide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred mixture of 3-iodo-1-propanol (4.3 g, 23 mmol) and imidazole (3.74 g, 55 mmol) in dimethylformamide (20 ml) was added tert-butylchlorodiphenylsilane (6.8 g, 24.7 mmol) at ambient temperature and the reaction mixture was stirred for 20 hours. The reaction mixture was then poured into cold water. The combined extracts were washed with dilute hydrochloric acid, 5 percent sodium bicarbonate dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography over silica gel eluted with CH2Cl2 :hexane (1:5, v:v) and further by distillation to afford the desired product as a colorless oil: b.p. 134°-5° C./0.01 mmHg.

後処理

  1. washThe combined extracts were washed with dilute hydrochloric acid, 5 percent sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography over silica gel
  5. washeluted with CH2Cl2 :hexane (1:5, v:v) and further by distillation

出典と根拠

ORDレコード
ord-18fda12598e749c5875a0df6582d5234
出典データセット
uspto-grants-1989_07
特許番号
US04847306

関連ノート

読み込み中…