Imidazole → 4-(2-{[tert-Butyl(dimethyl)silyl]oxy}propoxy)benzaldehyde

HRID 2362822노트

반응식

HRID 2362822 반응식
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[OH:14][CH:15]([CH3:26])[CH2:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Si:1]([O:14][CH:15]([CH3:26])[CH2:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 574320794-(2-Hydroxypropoxy)benzaldehyde

생성물 1

HCID 592019704-(2-{[tert-Butyl(dimethyl)silyl]oxy}propoxy)benzaldehyde

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5.39 g (35.7 mmol) of tert-butyldimethylsilyl chloride and 3.30 g (48.5 mmol) of imidazole are added successively to a solution of 4.60 g (25.5 mmol) of the compound from Example 40A in 120 ml of dry dimethylformamide, and the mixture is stirred at RT for 20 h. 100 ml of saturated sodium bicarbonate solution are then added, and the reaction mixture is extracted with diethyl ether (three times, 100 ml each). The combined organic phases are dried over magnesium sulphate. After removal of the solvent on a rotary evaporator, the crude product is purified chromatographically on silica gel 60 (mobile phase gradient cyclohexane/ethyl acetate 50:1→10:1).

후처리

  1. extractionthe reaction mixture is extracted with diethyl ether (three times, 100 ml each)
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. customAfter removal of the solvent
  4. customon a rotary evaporator
  5. customthe crude product is purified chromatographically on silica gel 60 (mobile phase gradient cyclohexane/ethyl acetate 50:1→10:1)

출처 및 근거

ORD 기록
ord-84321affe6be40f3a8a0e9fa0858ede9
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691850B2

반응 노트

불러오는 중…