Sodium hydride → Acetic acid, 2-(1,4-dioxaspiro(4.5)dec-8-ylidene)-, ethyl ester

To a suspension of NaH (60% mineral oil suspension, 33.3 g, 832.38 mmol) in anhydrous THF (1 L) was added a solution of 1,4-dioxaspiro[4.5]decan-8-one (100 g, 640.29 mmol) in anhydrous THF (500 mL) dropwise at 0° C. for 1 h and continued to stir for 1 h. Then triethyl phosphonoacetate (203.23 g, 832.38 mmol) was added to the above suspension dropwise at −20° C. in 1 h. The resulting mixture was allowed to warm to rt, stirred for 2 h, quenched with H2O (1 L) and extracted with EtOAC (1 L×3). The combined organic phases were washed with brine (1 L), dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/10) to give the title compound as pale yellow oil (157 g, 100%).

1. stirringstirred for 2 h
2. customquenched with H2O (1 L)
3. extractionextracted with EtOAC (1 L×3)
4. washThe combined organic phases were washed with brine (1 L)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/10)

ORDレコード

ord-fac7620a8fc549d489a18f5da5684021

出典データセット

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09399637B2