Water → Scopine Di(2-thienyl) Glycolate

HRID 14444Notes

Reaction equation

[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

Participants

Conditions

Temperature: 70 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-39e28322721a467dbee2fe70a9c2b8c6
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732441B2

Reaction notes

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