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

HRID 2362822ノート

反応式

HRID 2362822 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-84321affe6be40f3a8a0e9fa0858ede9
出典データセット
uspto-grants-2014_04
特許番号
US08691850B2

反応ノート

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