Acetic Anhydride → HCID 131728925, compound

Participants

Reaction Steps

Potassium acetate (2.56 g, 26.1 mmol) was added to a dimethylacetamide (25 mL) solution of 3-ethylhepta-2,6-dienoic acid (2.01 g, 13.0 mmol) and acetic anhydride (2.66 g, 26.1 mmol), and the mixture was stirred at room temperature for 1 hour and then stirred at 120° C. for 3 hours. The mixture was treated with an ice water solution, followed by extraction with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was applied to column chromatography to obtain a pale yellow oil substance. The substance obtained here was added to an acetonitrile (40 mL) solution of tert-butyl dimethylphosphonoacetate (2.60 g, 16.6 mmol), lithium chloride (0.70 g, 16.6 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.60 g, 16.6 mmol) stirred in advance for 1 hour, and the mixture was further stirred for 3.5 hours. The mixture was treated with water, and volatile portions were then distilled off under reduced pressure, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the compound of interest as a yellow oil substance (2.20 g, 68%).

Provenance & Evidence