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

HRID 1477960Notes

Reaction equation

HRID 1477960 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 373318Acetic acid, 2-(1,4-dioxaspiro(4.5)dec-8-ylidene)-, ethyl esterYield 216.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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. in 1 h and the reaction mixture was stirred for another 1 h. Then triethyl phosphonoacetate (203.23 g, 832.38 mmol) was added dropwise to the above suspension at −20° C. in 1 h. The resulting mixture was allowed to warm to rt, stirred for another 2 h, then 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%).

Workup

  1. stirringstirred for another 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)

Sources & evidence

ORD record
ord-8a5760312d17449394e5fba6cbddf0df
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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