Ethylene Glycol → 1,4-Dioxaspiro[4.5]decane-8-carbonitrile, 8-(4-fluorophenyl)-

HRID 2370293Notes

Reaction equation

HRID 2370293 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:15]#[N:16])[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:17](O)[CH2:18][OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:15]#[N:16])[CH2:9][CH2:10][C:11]3([O:19][CH2:18][CH2:17][O:14]3)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 918051-(4-Fluorophenyl)-4-oxocyclohexanecarbonitrile

Product 1

HCID 122302421,4-Dioxaspiro[4.5]decane-8-carbonitrile, 8-(4-fluorophenyl)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

25 g of 1-(4-Fluoro-phenyl)-4-oxo-cyclohexanecarbonitrile (73) were dissolved in 850 mL of toluene. 9 mL of ethylene glycol and 1.5 g of p-toluene sulfonic acid were added and the mixture was refluxed at a Dean-Stark apparatus for 6 h. The mixture was allowed to cool down to room temperature and extracted twice with saturated sodium bicarbonate solution and once with brine. The organic layer was dried over sodium sulfate and evaporated to dryness to give 30.15 g of crude product, that was sufficiently pure for further conversion. Rt=1.47 min (Method C). Detected mass: 262.2 (M+H+).

Workup

  1. temperaturethe mixture was refluxed at a Dean-Stark apparatus for 6 h
  2. extractionextracted twice with saturated sodium bicarbonate solution and once with brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-66661bc920ef41e2af12de7f8ebb9fd7
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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