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

HRID 1477950

Reaktionsgleichung

Reaktionsgleichung von HRID 1477950
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1>C1COCC1>[O:3]1[C:7]2([CH2:12][CH2:11][C:10](=[CH:8][C:7]([O:3][CH2:4][CH3:5])=[O:6])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Produkt 1

HCID 373318Acetic acid, 2-(1,4-dioxaspiro(4.5)dec-8-ylidene)-, ethyl esterAusbeute 216,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-57e41a973d294c82a0ad4decb78d7b44
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403801B2

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