Sodium hydride → Ethyl 6-oxaspiro[2.5]octane-1-carboxylate

HRID 656247Notes

Reaction equation

HRID 656247 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[O:9]1[CH2:14][CH2:13][C:12](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][CH2:10]1>CS(C)=O>[CH:15]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12]2([CH2:13][CH2:14][O:9][CH2:10][CH2:11]2)[CH2:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 11105795Ethyl 2-(oxan-4-ylidene)acetate

Product 1

HCID 57429837Ethyl 6-oxaspiro[2.5]octane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

51.93 g of sodium hydride (60% dispersion in oil) is taken up in 1100 ml of dry dimethyl sulphoxide under argon. 272 g of trimethylsulphoxonium iodide are added in portions over 20 minutes at room temperature, and the reaction mixture is then stirred at room temperature for 1.5 hours. 170.00 g of ethyl (tetrahydropyran-4-ylidene)acetate [130312-00-4] are added dropwise, and the reaction mixture is stirred at room temperature for 18 hours. The mixture is poured into ice and extracted with tert-butyl methyl ether. The combined organic extracts are washed with brine, dried with sodium sulphate and evaporated. The title compound is obtained as a colourless oil from the residue by vacuum distillation (68-70° C., 0.09 mbar). Rt=3.49 (Gradient I).

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 18 hours
  2. additionThe mixture is poured into ice
  3. extractionextracted with tert-butyl methyl ether
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried with sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-6c8f4705adf347a5b56006db9d641af0
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

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