Diethyl Ether → 8-Chloro-7-isopropoxy-4-isopropyl-2,2-dimethyl-2H-chromene-6-carbaldehyde
反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:16])[C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[O:8][C:7]([CH3:18])([CH3:17])[CH:6]=[C:5]2[CH:19]([CH3:21])[CH3:20].C([Li])CCC.[CH2:27]([O:29]CC)C>>[Cl:16][C:10]1[C:11]([O:12][CH:13]([CH3:15])[CH3:14])=[C:2]([CH:27]=[O:29])[CH:3]=[C:4]2[C:9]=1[O:8][C:7]([CH3:18])([CH3:17])[CH:6]=[C:5]2[CH:19]([CH3:21])[CH3:20]参加物
反応条件
- 温度
- -78 °C
実験手順
To a solution of 6-bromo-8-chloro-7-isopropoxy-4-isopropyl-2,2-dimethyl-2H-chromene, (Compound 21, 3.9 g, 10.3 mmol) in diethyl ether (100 mL) at −78° C. was added n-butyllithium (1.6 M in hexanes, 10.3 mL, 16.5 mmol). After stirring at −78° C. for 20 min, the reaction mixture was quenched with DMF (10 mL). After further stirring at −78° C. for 15 min, the reaction was allowed to warm to room temperature. The reaction mixture was poured into 1N HCl and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (silica gel, 100% hexanes to 2% ethyl acetate in hexanes) to afford the title compound as a colorless oil.
後処理
- customthe reaction mixture was quenched with DMF (10 mL)
- stirringAfter further stirring at −78° C. for 15 min
- temperatureto warm to room temperature
- additionThe reaction mixture was poured into 1N HCl
- extractionextracted with ethyl acetate
- washThe combined organic layers were washed with water and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude residue was purified by flash chromatography (silica gel, 100% hexanes to 2% ethyl acetate in hexanes)
出典と根拠
- ORDレコード
- ord-c814c10568e045ec9060f7061c454a38
- 出典データセット
- uspto-grants-2005_05
- 特許番号
- US06887896B1
反応ノート
読み込み中…