Methyl diethylphosphonoacetate → HCID 57706483, compound

Participants

Reaction Steps

To a solution of 2-cyclopropylethanol (20.72 g, 240.6 mmol) (commercially available from Alfa Aesar) in 5:1 ACN/DCM (480 mL) were added TEMPO (1.879 g, 12.03 mmol) (commercially available from Aldrich) and iodobenzene diacetate (81.36 g, 252.6 mmol) (commercially available from Aldrich) as solids. The resulting slurry was stirred overnight at room temperature to afford a homogeneous solution. The reaction mixture was used directly in the next step. To a suspension of lithium chloride (15.30 g, 360.9 mmol) in ACN (400 mL) were added methyl 2-(diethoxyphosphoryl)acetate (48.04 mL, 288.7 mmol) (commercially available from Aldrich) and DBU (115.1 mL, 769.9 mmol) (commercially available from Aldrich) at room temperature. The mixture was cooled to 0° C., and to it was added 2-cyclopropylacetaldehyde (20.24 g, 240.6 mmol) solution dropwise. The resulting cloudy mixture was warmed to room temperature and stirred overnight. The mixture was partitioned between water and EtOAc. The layers were separated, and the aqueous phase was extracted with additional EtOAc. The combined organics were washed with water and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford 89.A as a colorless liquid.

Provenance & Evidence