Sulfoxonium, trimethyl-, iodide (1:1) → 1-Oxaspiro[2.5]octane-6-carbonitrile

HRID 2045126Notes

Reaction equation

HRID 2045126 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]#[N:9])[CH2:4][CH2:3]1.[CH3:10]C(C)([O-])C.[K+].[I-].C[S+](C)(C)=O>CS(C)=O.[Cl-].[Na+].O>[O:1]1[C:2]2([CH2:7][CH2:6][CH:5]([C:8]#[N:9])[CH2:4][CH2:3]2)[CH2:10]1

Participants

6

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 122356394-Oxocyclohexane-1-carbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 866479041-Oxaspiro[2.5]octane-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 4-oxocyclohexanecarbonitrile (1.90 g) in dimethylsulfoxide (8 mL) was added dropwise to a solution of potassium t-butoxide (2.60 g) and trimethylsulfoxonium iodide (5.09 g) in dimethylsulfoxide (30 mL) at room temperature. The mixture was stirred overnight, diluted with 20% brine, and extracted with 3× ethyl acetate. The combined organic layers were washed with 20% brine, dried over Na2SO4, and concentrated. The crude was purified on a 40 g column using an ISCO Companion flash system eluting with hexane/ethyl acetate (6:4 to 5:5) to give the desired product.

Workup

  1. extractionextracted with 3× ethyl acetate
  2. washThe combined organic layers were washed with 20% brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude was purified on a 40 g column
  6. washeluting with hexane/ethyl acetate (6:4 to 5:5)

Sources & evidence

ORD record
ord-784ce25f6f914586bed743b93e141262
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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