Sodium Methoxide → Spiro[2.5]octane-5,7-dione

HRID 1503077Notes

Reaction equation

HRID 1503077 reaction equation
CO[C:3](=[O:12])[CH2:4][C:5]1([CH2:8][C:9](=[O:11])[CH3:10])[CH2:7][CH2:6]1.C[O-].[Na+]>O1CCCC1.CO.C(OC)(C)(C)C>[CH2:6]1[C:5]2([CH2:4][C:3](=[O:12])[CH2:10][C:9](=[O:11])[CH2:8]2)[CH2:7]1

Participants

6

Reactant 2

HCID 10942334Sodium MethoxideHCID 73052801HCID 73052801, compound

Product 1

HCID 55264674Spiro[2.5]octane-5,7-dione

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

23.3 g of crude [1-(2-oxo-propyl)-cyclopropyl]-acetic acid methyl ester (60% purity, from step 5) are dissolved in 135 ml of tetrahydrofuran and 17.1 g of a sodium methanolate solution in methanol (30% in methanol) are added at room temperature and the mixture is stirred for six hours. Then the solution is diluted with 135 ml of methyl tert-butyl ether and quenched with 135 ml of water. Stirring is continued for five minutes, then the phases are separated. The aqueous phase is extracted with 67.5 ml of methyl tert-butyl ether, then acidified to pH 2-3 with 37% HCl and washed twice with 67.5 ml of methyl tert-butyl ether each. The combined organic phases are washed with 18 ml of water and concentrated to dryness. The crude product is stirred with 18 ml of cold methyl tert-butyl ether and then the precipitate is isolated by filtration. The filter cake is washed with 18 ml of cold methyl tert-butyl ether to yield the product as an off-white solid.

Workup

  1. customquenched with 135 ml of water
  2. stirringStirring
  3. waitis continued for five minutes
  4. customthe phases are separated
  5. extractionThe aqueous phase is extracted with 67.5 ml of methyl tert-butyl ether
  6. washwashed twice with 67.5 ml of methyl tert-butyl ether each
  7. washThe combined organic phases are washed with 18 ml of water
  8. concentrationconcentrated to dryness
  9. stirringThe crude product is stirred with 18 ml of cold methyl tert-butyl ether
  10. customthe precipitate is isolated by filtration
  11. washThe filter cake is washed with 18 ml of cold methyl tert-butyl ether

Sources & evidence

ORD record
ord-69be6c9dfdbc466a96139ac8d15eabdc
Source dataset
uspto-grants-2015_12
Patent number
US09212120B2

Reaction notes

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