Sodium borohydride → (3-Chloroisoquinolin-4-yl)methanol
反応式
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[CH:12]=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[CH2:12][OH:13])=[CH:9][CH:8]=[CH:7][CH:6]=2参加物
4
反応条件
- 温度
- 0 °C
実験手順
To 3-chloroisoquinoline-4-carbaldehyde (220 mg, crude) in THF (10 mL) was added NaBH4 (155 mg, 4.08 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h, acidified to pH 3, and extracted with EtOAc. The combined organic layers were washed with saturated sodium bicarbonate solution and brine, dried over Na2SO4, filtered, and concentrated to give a crude solid. The crude was purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-chloroisoquinolin-4-yl)methanol (92 mg, 24% for three steps). LRMS (M+H+) m/z 194.0.
後処理
- extractionextracted with EtOAc
- washThe combined organic layers were washed with saturated sodium bicarbonate solution and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customto give a crude solid
- customThe crude was purified on silica gel using
- additiona mixture of EtOAc and hexanes as eluent
出典と根拠
- ORDレコード
- ord-a3441693e3294eb1915e45af405a3315
- 出典データセット
- uspto-grants-2015_04
- 特許番号
- US09012450B2
反応ノート
読み込み中…