Lithium Bromide → HCID 56619555, compound
Reaction equation
[CH2:1]([O:3][P:4]([O:23][CH2:24][CH3:25])([CH:6]1[CH2:10][CH2:9][CH:8]([CH2:11]OS(C2C=CC(C)=CC=2)(=O)=O)[O:7]1)=[O:5])[CH3:2].[Br-:26].[Li+]>CN(C=O)C>[Br:26][CH2:11][C@@H:8]1[O:7][C@@H:6]([P:4]([O:23][CH2:24][CH3:25])([O:3][CH2:1][CH3:2])=[O:5])[CH2:10][CH2:9]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a stirring solution of (±)-2-diethoxyphosphinoyl-5-(p-toluenesulfonyloxymethyl)-tetrahydrofuran (example 60) (12.0 g, 30.61 mmol) in dry DMF (60 mL) was added anhydrous lithium bromide (13.3 g, 153.05 mmol). The solution was then stirred at 80° C. for 4 h. The mixture was cooled and concentrated to dryness under reduced pressure. The residue was then dissolved in methylene chloride and the solution was washed with water (2×50 mL), brine (50 mL), dried (MgSO4) and concentrated. The cis-trans mixture was separated by flash chromatography eluting with 10→20% acetone in hexanes.
Workup
- temperatureThe mixture was cooled
- concentrationconcentrated to dryness under reduced pressure
- dissolutionThe residue was then dissolved in methylene chloride
- washthe solution was washed with water (2×50 mL), brine (50 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe cis-trans mixture was separated by flash chromatography
- washeluting with 10→20% acetone in hexanes
Sources & evidence
- ORD record
- ord-824d075a6d3d42759ec0522e6357de56
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06127540
Reaction notes
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