Ethyl Acetate → 8-Methylidene-1,4-dioxaspiro[4.5]decane

HRID 1966812Notes

Reaction equation

HRID 1966812 reaction equation
[CH3:1]C(C)([O-])C.[K+].CI.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:28]1[C:32]2([CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]2)[O:31][CH2:30][CH2:29]1.C(OCC)(=O)C>O1CCCC1.O>[CH2:1]=[C:35]1[CH2:36][CH2:37][C:32]2([O:31][CH2:30][CH2:29][O:28]2)[CH2:33][CH2:34]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 13401130HCID 13401130, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 109537438-Methylidene-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Potassium tert-butoxide (3.230 gm, 28.812 mmol) and triphenylphosphine methyl iodide (10.286 gm, 28.812 mmol) were dissolved in dry tetrahydrofuran (30 ml). The mixture was cooled to −78° C. and stirred at the same temperature for about 15 minutes. 1,4-Dioxaspiro[4.5]decan-8-one (3.0 gm, 19.208 mmol) in tetrahydrofuran was added drop wise and the mixture was stirred at the same temperature for about 30 minutes and then it was warmed to room temperature and stirred overnight, extaction was done with ethyl acetate and water. The organic layer was dried over sodium sulphate and concentrated. Purification was done by column chromatography.

Workup

  1. stirringthe mixture was stirred at the same temperature for about 30 minutes
  2. temperatureit was warmed to room temperature
  3. stirringstirred overnight
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-a70918488f4a43a5a602075749591145
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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