Ethylene Glycol → HCID 86729363, compound

HRID 521202Notes

Reaction equation

HRID 521202 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]#[N:9])[CH:4]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:3]1.C1C=CC=CC=1.[CH2:25](O)[CH2:26][OH:27].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOC(C)=O>[C:13]1([S:10]([CH:4]2[CH:5]([C:8]#[N:9])[CH2:6][CH2:7][C:2]3([O:27][CH2:26][CH2:25][O:1]3)[CH2:3]2)(=[O:12])=[O:11])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 85385994HCID 85385994, compound

Product 1

HCID 86729363HCID 86729363, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a pressure vessel was added (1R,2S and 1S,2R)-4-oxo-2-(phenylsulfonyl) cyclohexanecarbonitrile (100 mg, 0.380 mmol), benzene (19.0 mL), ethylene glycol (0.90 mL, 16 mmol), and p-toluenesulfonic acid monohydrate (14 mg, 0.076 mmol). The vessel was capped and the reaction mixture was heated to reflux and allowed to stir for 16 hours. The reaction mixture was allowed to cool to ambient temperature before it was diluted with EtOAc. The organic layer was washed with water (3×), brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo (23° C. water bath) to afford (7S,8R and 7R,8S)-7-(phenylsulfonyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile as a crude residue. To the crude residue (110 mg, 0.358 mmol) was added THF (7.1 mL) and potassium tert-butoxide (137 mg, 1.22 mmol). The reaction mixture was allowed to stir at ambient temperature for 15 minutes before it was diluted with diethyl ether. The organic layer was washed with water, brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo (23° C. water bath) to afford the title compound.

Workup

  1. customThe vessel was capped
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux
  4. washThe organic layer was washed with water (3×), brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo (23° C. water bath)

Sources & evidence

ORD record
ord-7ba59d5782814c62bc6ee2e3158cd721
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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