Iodoethane → Tert-butyl 2-(diethoxyphosphoryl)butyrate

HRID 517315Notes

Reaction equation

HRID 517315 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH2:7][P:8]([O:13][CH2:14][CH3:15])([O:10][CH2:11][CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:19](I)[CH3:20]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:16])[CH:7]([P:8]([O:10][CH2:11][CH3:12])([O:13][CH2:14][CH3:15])=[O:9])[CH2:19][CH3:20])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 21082801Tert-butyl 2-(diethoxyphosphoryl)butyrateYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diethylphosphonoacetic acid tert-butyl ester (1.0 g, 4.0 mmol) was dissolved in N,N-dimethylformamide (1.4 and 60% sodium hydride (0.17 g, 4.4 mmol) was added at 0° C. After stirring at room temperature for 30 minutes, the reaction mixture was cooled again to 0° C., ethyl iodide (0.33 mL, 4.1 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed successively with 0.5N hydrochloric acid, water and saturated brine, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=57/43) to give the title compound (0.92 g, 3.3 mmol, 83%).

Workup

  1. additionwas added at 0° C
  2. temperaturethe reaction mixture was cooled again to 0° C.
  3. stirringthe mixture was stirred at room temperature overnight
  4. washwashed successively with 0.5N hydrochloric acid, water and saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=57/43)

Sources & evidence

ORD record
ord-420e509b318a4bfabf2548095802a895
Source dataset
uspto-grants-2015_08
Patent number
US09115107B2

Reaction notes

Loading…