Tetrahydrofuran → (4-Ethylphenyl)(3-hydroxy-4-pyridinyl)methanone

反応式

C[Si](C)(C)CCOC[O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.O.[C:17]1(C)[CH:22]=C[C:20](S(O)(=O)=O)=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+].[O:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>>[CH2:19]([C:18]1[CH:17]=[CH:22][C:36]([C:37]([C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[OH:7])=[O:33])=[CH:35][CH:34]=1)[CH3:20]

参加物

反応物 4

HCID 8028Tetrahydrofuran

HCID 516892Sodium Bicarbonate

HCID 521998p-Toluenesulfonic acid monohydrate

HCID 15635484HCID 15635484、化合物

生成物 1

HCID 23103597(4-Ethylphenyl)(3-hydroxy-4-pyridinyl)methanone収率 83%

反応条件

温度: 80 °C

実験手順

Next, a mixture of 4-(4-ethylbenzoyl)-[3-[2-(trimethylsilyl)ethoxymethoxy]pyridine (3.4 g), p-toluenesulfonic acid monohydrate (3.46 g, 18.2 mmol) and tetrahydrofuran (60 mL) was stirred at 80° C. for 2 hours. After cooling to room temperature, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50) to give the titled compound (1.57 g, 83%).