Heptane → HCID 178444500, compound

HRID 395936Notes

Reaction equation

HRID 395936 reaction equation
Cl[C:2]([F:7])([F:6])[C:3]([O-])=O.[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:28]([C@H:33]1[CH2:38][CH2:37][C@H:36]([C@H:39]2[CH2:44][CH2:43][C@H:42]([C:45](=O)C)[CH2:41][CH2:40]2)[CH2:35][CH2:34]1)[CH2:29][CH2:30][CH2:31][CH3:32].CCCCCCC>CN(C=O)C>[F:6][C:2]([F:7])=[CH:3][CH2:45][C@H:42]1[CH2:43][CH2:44][C@H:39]([C@H:36]2[CH2:37][CH2:38][C@H:33]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:34][CH2:35]2)[CH2:40][CH2:41]1

Participants

6

Reactant 4

HCID 8900HeptaneHCID 11776TriphenylphosphineHCID 2734985Sodium chlorodifluoroacetateHCID 178444505HCID 178444505, compound

Product 1

HCID 178444500HCID 178444500, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A nitrogen-purged 1-L three-neck flask equipped with a stirrer, a thermometer and a dropping funnel was charged with 16.4 g (107.7 mmol) of sodium chlorodifluoroacetate, 28.3 g (107.7 mmol) of triphenylphosphine and 200 ml of DMF, and the mixture was heated up to 80° C. while stirring. A solution of 15.0 g (53.9 mmol) of 1-(trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl)acetaldehyde dissolved in 100 ml of DMF was added dropwise at 80 to 110° C., and the solution was stirred at 100° C. for 2 hours. The reaction mixture was transferred into a 2-L beaker, and 500 ml of heptane was added thereto. Insoluble materials were separated by filtration by means of a glass filter, and 300 ml of water was added thereto. The separated heptane layer was washed twice with 300 ml of water and dried over anhydrous magnesium sulfate. The solvent was distilled of under reduced pressure, and then the concentrated residue was purified by means of a silica gel column chromatography with heptane as a developing solvent to obtain 14.1 g of 1,1-difluoro-3-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)-1-propene.

Workup

  1. customA nitrogen-purged 1-L three-neck flask
  2. customequipped with a stirrer
  3. additionwas added dropwise at 80 to 110° C.
  4. stirringthe solution was stirred at 100° C. for 2 hours
  5. additionwas added
  6. customInsoluble materials were separated by filtration by means of a glass
  7. filtrationfilter
  8. addition300 ml of water was added
  9. washThe separated heptane layer was washed twice with 300 ml of water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationThe solvent was distilled of under reduced pressure
  12. customthe concentrated residue was purified by means of a silica gel column chromatography with heptane as a developing solvent

Sources & evidence

ORD record
ord-00860d541bc0486195072448b6b32ace
Source dataset
uspto-grants-2003_08
Patent number
US06605747B2

Reaction notes

Loading…