Lithium Bromide → HCID 56619555, compound

HRID 636879Notes

Reaction equation

HRID 636879 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]1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 21255867(+/-)-2-Diethoxyphosphinoyl-5-(p-Toluenesulfonyloxymethyl)-Tetrahydrofuran

Product 1

HCID 56619555HCID 56619555, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated to dryness under reduced pressure
  3. dissolutionThe residue was then dissolved in methylene chloride
  4. washthe solution was washed with water (2×50 mL), brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe cis-trans mixture was separated by flash chromatography
  8. washeluting with 10→20% acetone in hexanes

Sources & evidence

ORD record
ord-3c48a467202742058a4861f26ed1faac
Source dataset
uspto-grants-2001_02
Patent number
US06194576B1

Reaction notes

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