Cycloheptanone → 1-oxaspiro[2.6]nonane

HRID 1778892Notes

Reaction equation

HRID 1778892 reaction equation
[I-].C[S+](C)C.[C:6]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:14]C(C)([O-])C.[K+]>CS(C)=O>[O:13]1[C:6]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:14]1

Participants

5

Reactant 3

HCID 10400CycloheptanoneHCID 75127Trimethylsulfonium iodideHCID 23665647Potassium tert-butoxide

Product 1

HCID 6429411-oxaspiro[2.6]nonane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a mixture of trimethylsulfonium iodide (35.7 g) in 300 mL dry DMSO was added 11.2 g of cycloheptanone with stirring. A solution of potassium tert-butoxide (16.83 g) in 200 mL dry DMSO was slowly added. The resulting solution was stirred at room temperature for 16 hours. The reaction mixture was quenched by addition of water (600 mL), and extracted with diethyl ether (3×200 mL). The combined organic layers were washed with water (200 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give the product.

Workup

  1. stirringThe resulting solution was stirred at room temperature for 16 hours
  2. customThe reaction mixture was quenched by addition of water (600 mL)
  3. extractionextracted with diethyl ether (3×200 mL)
  4. washThe combined organic layers were washed with water (200 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the product

Sources & evidence

ORD record
ord-988589e00877493eb98baf48cf2a1bfe
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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