Triethyl phosphonoacetate → HCID 178471800, compound

To a solution (600 ml) of ethyl 4-oxocyclohexanecarboxylate (150 g) in ethanol was added sodium hydroxide (38.8 g) with stirring at room temperature. The reaction solution was stirred for 1 hr and ethyl diethylphosphonoacetate (192 ml) was added. To this reaction solution was added dropwise 21% sodium ethoxide/ethanol solution (363 ml) with stirring under ice-cooling over 1 hr. The stirring was continued for 1 hr and acetic acid (126 ml) was added. Then ammonium formate (111 g) and palladium carbon (5%, 15 g) were added and the mixture was stirred at 60° C. for 6 hr with heating. The reaction solution was allowed to return to room temperature and insoluble materials were filtered off through celite. The filtrate was concentrated and the obtained residue was diluted with ethyl acetate. The mixture was washed successively with 2N aqueous hydrochloric acid, water and saturated brine. The organic layer was dried over sodium sulfate and sodium sulfate was filtered off. The filtrate was concentrated to give a crudely purified product (180.4 g) of the title compound.

1. stirringThe reaction solution was stirred for 1 hr
2. stirringwith stirring under ice-
3. temperaturecooling over 1 hr
4. stirringthe mixture was stirred at 60° C. for 6 hr
5. temperaturewith heating
6. customto return to room temperature
7. filtrationinsoluble materials were filtered off through celite
8. concentrationThe filtrate was concentrated
9. additionthe obtained residue was diluted with ethyl acetate
10. washThe mixture was washed successively with 2N aqueous hydrochloric acid, water and saturated brine
11. dry with materialThe organic layer was dried over sodium sulfate and sodium sulfate
12. filtrationwas filtered off
13. concentrationThe filtrate was concentrated

ORD record

ord-5ce172b7b45740f4830bf7f1241b9726

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807701B2