Acetonitrile → HCID 22715202, compound

HRID 352088Notes

Reaction equation

HRID 352088 reaction equation
[CH:1]([O:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]1)=[CH2:2].[C:13](#N)C.[Cl:16][C:17]([F:21])=[C:18]([F:20])[F:19]>C([O-])([O-])=O.[Cs+].[Cs+].O>[Cl:16][C:17]([F:21])([CH3:13])[C:18]([F:20])([F:19])[O:12][CH2:11][CH:8]1[CH2:9][CH2:10][CH:5]([CH2:4][O:3][CH:1]=[CH2:2])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 6594ChlorotrifluoroethyleneHCID 163934Cyclohexanemethanol, 4-[(ethenyloxy)methyl]-

Product 1

HCID 22715202HCID 22715202, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 10796Cesium carbonateCatalystHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

Into a 450 mL capacity PARR® reactor, 1,.4-cyclohexanedimethanol vinyl ether (50 g, 294 mmol), acetonitrile (100 mL), and Cs2CO3 (2 g, 6 mmol) were added. The PARR® reactor was cooled to ˜30° C., partially evacuated and chlorotrifluoroethylene (34 g, 294 mmol) was condensed and the resultant mixture was heated at ˜50-60° C with stirring for 3 hours. After this, the PARR® reactor was cooled to room temperature, vented in the fume hood and the reaction mixture was poured into ˜150 mL water and the lower layer containing the crude product separated, and was concentrated under reduced pressure 0.05 mmHg) at 25-30° C. to afford the desired product as a colorless viscous liquid (49 g, 58% yield) which is a mixture of cis/trans isomers in the ratio 73:18; refractive index of 1.415 at 23.7° C.; GC/MS (EI mode): m/z at 286 for M+; 19F and 1H NMR spectral data are consistent with the structure.

Workup

  1. custompartially evacuated
  2. customcondensed
  3. temperatureAfter this, the PARR® reactor was cooled to room temperature
  4. customseparated
  5. concentrationwas concentrated under reduced pressure 0.05 mmHg) at 25-30° C.

Sources & evidence

ORD record
ord-1711970a47774366af95222e22a27154
Source dataset
uspto-grants-2004_06
Patent number
US06743943B2

Reaction notes

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