Ethyl Bromide → 2-[2-(2,5-Dimethylphenoxymethyl)-alpha-hydroxybenzyl]pyridine
反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[CH3:17].[Mg].Br[CH2:20][CH3:21].[Cl-].[NH4+:23].[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1>>[CH3:17][C:11]1[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:10]=1[O:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:26]([C:25]1[CH:24]=[CH:28][CH:21]=[CH:20][N:23]=1)[OH:27]参加物
反応条件
- 温度
- 52.5 °C
実験手順
A mixture of 2.91 g (0.01 mol) of 1-bromo-2-(2,5-dimethylphenoxymethyl) benzene and 8 ml of THF was added to a suspension of 0.36 g (0.015 mol) of magnesium, 0.1 ml of bromoethane, and 2 ml of tetrahydrofuran at 45 to 55° C. over 5 minutes under a nitrogen gas atmosphere and stirred at 50 to 55° C. for an hour to prepare a Grignard's reagent. The Grignard's reagent was added to a mixture of 1.18 g (0.011 mol) of 2-pyridinecarboxyaldehyde and 10 ml of THF below 5° C. over 15 minutes and stirred at room temperature for 2 hours. After completion of the reaction, 150 ml of an aqueous solution of ammonium chloride was added and extracted with 150 ml of ether. After the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, the residue thus obtained was purified by column chromatography on silica gel (ethyl acetate/n-hexane) to give 2.42 g of 2-[2-(2,5-dimethylphenoxymethyl)-α-hydroxybenzyl]pyridine (75.8% yield) as colorless oil.
後処理
- customto prepare a Grignard's reagent
- stirringstirred at room temperature for 2 hours
- additionwas added
- extractionextracted with 150 ml of ether
- dry with materialAfter the extract was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customthe residue thus obtained
- customwas purified by column chromatography on silica gel (ethyl acetate/n-hexane)
出典と根拠
- ORDレコード
- ord-8a16109aaa8949929118aa8335f800c7
- 出典データセット
- uspto-grants-2001_12
- 特許番号
- US06329371B1
反応ノート
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