Ethyl Bromide → 2-[2-(2,5-Dimethylphenoxymethyl)-alpha-hydroxybenzyl]pyridine
반응식
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].Br[CH2:19][CH3:20].[Cl-].[NH4+:22].[CH2:23]1[CH2:27][O:26][CH2:25][CH2:24]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:25]([C:24]1[CH:23]=[CH:27][CH:20]=[CH:19][N:22]=1)[OH:26]참가 물질
반응 조건
- 온도
- 52.5 °C
실험 절차
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 agnesium, 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.
후처리
- 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)
출처 및 근거
- ORD 기록
- ord-7d70990380cc49d0b1ea35d0efc034d7
- 출처 데이터셋
- uspto-grants-1999_10
- 특허 번호
- US05965740
반응 노트
불러오는 중…