4-Ethylbenzaldehyde → HCID 69220218、化合物

HRID 2116482ノート

反応式

HRID 2116482 の反応式
[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.CCCCC.C([Li])(C)(C)C.[CH2:26]([C:28]1[CH:35]=[CH:34][C:31]([CH:32]=[O:33])=[CH:30][CH:29]=1)[CH3:27].[Cl-].[NH4+]>CCOCC.O1CCCC1>[CH2:26]([C:28]1[CH:35]=[CH:34][C:31]([CH:32]([C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[O:7][CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:15])([CH3:14])[CH3:1])[OH:33])=[CH:30][CH:29]=1)[CH3:27]

参加物

7

反応物 4

HCID 208614-EthylbenzaldehydeHCID 25517Ammonium ChlorideHCID 15635484HCID 15635484、化合物HCID 178446069HCID 178446069、化合物

生成物 1

HCID 69220218HCID 69220218、化合物収率 55%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

Next, to a mixture of 3-[2-(trimethylsilyl)ethoxymethoxy]pyridine (23.0 g, 102 mmol) and tetrahydrofuran (400 ml), a 1.47 mol/L t-butyllithium n-pentane solution (80 ml, 118 mmol) was added dropwise at −70° C. over 25 minutes. After stirring at −70° C. for 1 hour, an ether solution of 4-ethylbenzaldehyde (17.7 g, 132 mmol) was added over 25 minutes. The reaction mixture was stirred at −70° C. for 2 hours and at room temperature for 2 hours. After warming to room temperature, the reaction mixture was poured into saturated aqueous ammonium chloride and extracted with ether. The organic layer was 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 (4-ethylphenyl)-[3-[2-(trimethylsilyl)ethoxymethoxy]pyridin-4-yl]-methanol (20.1 g, 55%) as a light-yellow powder.

後処理

  1. stirringThe reaction mixture was stirred at −70° C. for 2 hours and at room temperature for 2 hours
  2. temperatureAfter warming to room temperature
  3. extractionextracted with ether
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50)

出典と根拠

ORDレコード
ord-09f204d42e804c489412282411e3cc7d
出典データセット
uspto-grants-2008_10
特許番号
US07439232B2

反応ノート

読み込み中…