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

HRID 1477950

Reaction equation

HRID 1477950 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. 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%).

Workup

  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)

Sources & evidence

ORD record
ord-57e41a973d294c82a0ad4decb78d7b44
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Linked notes

Loading…