Ammonium Chloride → (2S)-2-benzyloxy-5-phenylpentan-3-ol
反応式
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+].C(=O)=O.CC(C)=O.[CH2:19]([O:26][C@@H:27]([CH3:31])[CH:28]1[O:30][CH2:29]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C.[Cu](Cl)Cl>[CH2:19]([O:26][C@H:27]([CH:28]([OH:30])[CH2:29][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:31])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1参加物
反応物 5
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- -78 °C
実験手順
A solution of 2.0M benzylmagnesium chloride in tetrahydrofuran (2.38 ml) was added dropwise to a stirred mixture of lithium chloride (20.2 mg) and copper(II) chloride (32 mg) in tetrahydrofuran (10 ml) at −78° C. (dry-ice/acetone) for a period of 10 minutes under nitrogen atmosphere. A solution of (3S)-3-benzyloxy-1,2-epoxybutane (obtained in Preparation 9) (425 mg) in tetrahydrofuran (10 ml) was added dropwise to this mixture at −78° C. over 10 minutes. The resulting mixture was stirred at −78° C. for 2.5 hours and then allowed to warm to room temperature, and stirred overnight. The reaction mixture was treated with saturated ammonium chloride solution (20 ml) at an ice-bath temperature, and then diluted with ethyl acetate (100 ml). The organic layer was washed with H2O (50 ml) and brine (50 ml), dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel (20 g) chromatography eluted with hexane/ethyl acetate (10:1) to give (2S)-2-benzyloxy-5-phenylpentan-3-ol (620 mg).
後処理
- temperatureto warm to room temperature
- stirringstirred overnight
- washThe organic layer was washed with H2O (50 ml) and brine (50 ml)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel (20 g) chromatography
- washeluted with hexane/ethyl acetate (10:1)
出典と根拠
- ORDレコード
- ord-40f12b4583f445faa7ef1a05a260b196
- 出典データセット
- uspto-grants-2002_03
- 特許番号
- US06359145B1
反応ノート
読み込み中…