Ethyl Acetoacetate → HCID 86735725, compound

Temperature

0 °C

A solution of 1.742 g of ethyl acetylacetate in 5 ml of tetrahydrofuran was slowly added to a mixture of 672mg of sodium hydride in a 50% oil mixture in 10 ml of tetrahydrofuran cooled to 0° C and the mixture was held at 0° C for 30 minutes. 8.7 ml of 1.6N butyllithium in hexane was added dropwise at 0° C to the reaction mixture and after standing at 0° C for 30 minutes, the mixture was cooled to -60° C. A solution of 2.3 g of the product of Step B in 5 ml of anhydrous tetrahydrofuran was added to the mixture and the mixture was held at -60° C for 3 hours and then overnight at -20° C. The mixture was poured into an iced monosodium phosphate solution and was extracted with ethyl acetate. The extracts were washed, dried and evaporated to dryness to obtain a yellow oil residue. The latter was chromatographed over silica gel and was eluted with an 80-20-2 cyclohexane-ethyl acetate-triethylamine mixture to obtain 1.47 g of ethyl (6E) 8,9-epoxy-3-oxo-6-nonenoate in the form of an oil.

1. waitafter standing at 0° C for 30 minutes
2. temperaturethe mixture was cooled to -60° C
3. waitthe mixture was held at -60° C for 3 hours
4. customovernight
5. customat -20° C
6. extractionwas extracted with ethyl acetate
7. washThe extracts were washed
8. customdried
9. customevaporated to dryness
10. customto obtain a yellow oil residue
11. customThe latter was chromatographed over silica gel
12. washwas eluted with an 80-20-2 cyclohexane-ethyl acetate-triethylamine mixture

ORD record

ord-7e63ad1b083447019a8984be3388190d

Source dataset

uspto-grants-1978_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04091226