Water → Scopine Di(2-thienyl) Glycolate

HRID 900217ノート

反応式

HRID 900217 の反応式
[CH3:1][N:2]1[CH:7]2[CH2:8][CH:9]([OH:11])[CH2:10][CH:3]1[CH:4]1[CH:6]2[O:5]1.C[O:13][C:14](=O)[C:15]([OH:26])([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)[C:16]1[S:17][CH:18]=[CH:19][CH:20]=1.[H-].[Na+].O>ClCCl>[CH3:1][N:2]1[CH:7]2[CH2:8][CH:9]([O:11][C:14](=[O:13])[C:15]([OH:26])([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[CH2:10][CH:3]1[CH:4]1[CH:6]2[O:5]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2744399-Methyl-3-oxa-9-azatricyclo(3.3.1.02,4)nonan-7-olHCID 11414137Methyl alpha-hydroxy-alpha-2-thienyl-2-thiopheneacetate

生成物 1

HCID 23553456Scopine Di(2-thienyl) Glycolate収率 42%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

The product of step (b) (2.00 g, 12.9 mmol) and the product of step (a) (3.61 g, 14.2 mmol) were melted together at 70° C., under a vacuum of 210 Torr for 1 h. Sodium hydride (60% suspension in oil, 620 mg, 15.5 mmol) was added and the reaction mixture was stirred at 70° C. under 210 Torr for 3 h. The reaction mixture was allowed to cool to ambient temperature and then water (30 mL) and dichloromethane (30 mL) were added. The organic layer was separated and washed with water (2×20 mL), dried (magnesium sulfate), filtered and the solvent was removed under reduced pressure. The resulting residue was purified by flash chromatography (5% MeOH/DCM) to give the title compound as a solid (2.03 g, 5.4 mmol, 42%).

後処理

  1. temperatureto cool to ambient temperature
  2. customThe organic layer was separated
  3. washwashed with water (2×20 mL)
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting residue was purified by flash chromatography (5% MeOH/DCM)

出典と根拠

ORDレコード
ord-eaa1717b89134882bf88a02155079783
出典データセット
uspto-grants-2008_04
特許番号
US07358244B2

反応ノート

読み込み中…