Water → 2-(3{[tert-Butyl(dimethyl)silyl]oxy}propyl)-1H-benzimidazole

HRID 1610796

반응식

HRID 1610796 반응식
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][CH2:10][CH2:11][CH2:12][C:13]1[NH:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1.C(N(CC)CC)C.O>CN(C=O)C>[Si:1]([O:9][CH2:10][CH2:11][CH2:12][C:13]1[NH:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 754702-Benzimidazolepropanol

생성물 1

HCID 695919622-(3{[tert-Butyl(dimethyl)silyl]oxy}propyl)-1H-benzimidazole수율 97.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To this end, tert-butyldimethylsilyl chloride (TBDMSCI) (14.68 g, 97.37 mmol) was added a little at a time to a solution of 2-(3-hydroxypropyl)-benzimidazole (15.60 g, 88.52 mmol) in DMF (265 ml) and triethylamine (20.27 ml, 145.41 mmol). The mixture was stirred at RT overnight and then admixed with water (800 ml) and extracted with diethyl ether. The organic phase was dried over sodium sulphate and chromatographed over silica gel (mobile phase: cyclohexane/ethyl acetate=6:1), giving 25 g (97%) of colourless crystals. MS (DCI): 291 (M+H)+

후처리

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customchromatographed over silica gel (mobile phase: cyclohexane/ethyl acetate=6:1)

출처 및 근거

ORD 기록
ord-fcb477d18a744f849491a493dcf7f30a
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06984642B1

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