Acetic Acid → Methyl 6-oxospiro[4.5]decane-7-carboxylate

HRID 539930Notes

Reaction equation

HRID 539930 reaction equation
[H-].[Na+].CO[C:5](=[O:8])[O:6][CH3:7].[CH2:9]1[C:13]2([C:18](=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:12][CH2:11][CH2:10]1.CC(O)=O>C1COCC1>[O:19]=[C:18]1[CH:17]([C:5]([O:6][CH3:7])=[O:8])[CH2:16][CH2:15][CH2:14][C:13]21[CH2:9][CH2:10][CH2:11][CH2:12]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 290662Spiro(4.5)decan-6-one

Product 1

HCID 57429459Methyl 6-oxospiro[4.5]decane-7-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

In a flask containing NaH (4.73 g, 118.20 mmol) in THF (30 mL) was added dimethylcarbonate (8.30 mL, 98.52 mmol). The mixture was heated at 80° C. To the mixture was added a solution of spiro[4.5]decan-10-one, 59, (6.00 g, 39.41 mmol) in THF dropwise (25 mL). The reaction was heated for 6 hrs at 80° C. The mixture was cooled to room temperature and hydrolyzed with AcOH. The solvent was evaporated and the crude residue was diluted with water and extracted with EtOAc. The organic layer was washed with aqueous saturated NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo.

Workup

  1. temperatureThe reaction was heated for 6 hrs at 80° C
  2. customThe solvent was evaporated
  3. additionthe crude residue was diluted with water
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with aqueous saturated NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-739dd15d0dff49a6b9eae07336c4e5d7
Source dataset
uspto-grants-2014_10
Patent number
US08871774B2

Reaction notes

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