Cyclopropyl methyl ketone → 1,3-Dicyclopropylpropane-1,3-dione

Temperature

52.5 °C

Cyclopropyl methyl ketone (2.5 mL; 25 mmol) was dissolved in DMSO (12.5 mL) and methyl cyclopropanecarboxylate (5.0 mL; 50 mmol; 2 equiv) was added. The reaction mixture was cooled in ice-water and sodium methoxide (2.70 g; 50 mmol; 2 equiv) was added. The reaction mixture was stirred for 5 min in the ice-water bath, the bath was removed, and the mixture was heated to 50-55° C. for 8 h. The reaction mixture was diluted with toluene (12.5 mL), cooled in ice-water, and 6 N HCl (9 mL) was added dropwise such that the temperature remained below 25 ° C. The layers were separated and the aqueous solution was extracted with additional toluene (10 mL). The combined organic solution was washed with aqueous sodium bicarbonate (10 mL), dried with sodium sulfate and concentrated to afford 3.50 g (92%) yield of 1,3-dicyclopropyl-1,3-propanedione.

1. customthe bath was removed
2. additionThe reaction mixture was diluted with toluene (12.5 mL)
3. temperaturecooled in ice-water
4. addition6 N HCl (9 mL) was added dropwise such that the temperature
5. customremained below 25 ° C
6. customThe layers were separated
7. extractionthe aqueous solution was extracted with additional toluene (10 mL)
8. washThe combined organic solution was washed with aqueous sodium bicarbonate (10 mL)
9. dry with materialdried with sodium sulfate
10. concentrationconcentrated

ORD record

ord-220af362724d4d6aa501c1aad57b12ae

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06143935