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

HRID 1610796

反応式

HRID 1610796 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)+

後処理

  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)

出典と根拠

ORDレコード
ord-fcb477d18a744f849491a493dcf7f30a
出典データセット
uspto-grants-2006_01
特許番号
US06984642B1

関連ノート

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