Sulfoxonium, trimethyl-, iodide (1:1) → 1,7,10-Trioxadispiro(2.2.4^(6).2^(3))dodecane

HRID 922115Notes

Reaction equation

HRID 922115 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.[I-].[CH3:13][S+](C)(C)=O.CC(C)([O-])C.[K+]>ClCCl>[O:10]1[C:7]2([CH2:6][CH2:5][C:4]3([O:3][CH2:2][CH2:1][O:11]3)[CH2:9][CH2:8]2)[CH2:13]1

Participants

5

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 120759531,7,10-Trioxadispiro(2.2.4^(6).2^(3))dodecane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 30.0 g (192 mmol) of 1,4-cyclohexanedione monoethlene acetal in 750 ml of dichloromethane was added to a homogeneous mixture of 50.7 g (231 mmol) of trimethylsulphoxonium iodide and 25.9 g (231 mmol) of potassium tert-butoxide, and the reaction mixture was stirred at room temperature for one hour. Ice-water was added, the phases were separated, the aqueous phase was extracted repeatedly with dichloromethane and the combined organic phases were washed repeatedly with water, dried over sodium sulphate, filtered and concentrated. This gave 28.3 g (87% of theory) of the title compound.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted repeatedly with dichloromethane
  3. washthe combined organic phases were washed repeatedly with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2ae76883acae413a9570cf6f22926c87
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

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