Imidazole → 1-(tert-Butyldiphenylsilyloxy)propyl iodide

HRID 231603

반응식

HRID 231603 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 198228821-(tert-Butyldiphenylsilyloxy)propyl iodide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-18fda12598e749c5875a0df6582d5234
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04847306

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