Sodium bis(2-methoxyethoxy)aluminiumhydride → HCID 178448059, compound

HRID 2081155Notes

Reaction equation

HRID 2081155 reaction equation
[F:1][C:2](F)=[CH:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1(C)C=CC=CC=1>[F:1]/[CH:2]=[CH:3]/[C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 178448060HCID 178448060, compound

Product 1

HCID 178448059HCID 178448059, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To trans-1-(2,2-difluoro-1-ethenyl)-4-(trans-4-propylcyclohexyl)cyclohexane (44.0 g, 0.16 mol) were added toluene (250 ml) and a 70 wt. % toluene solution of sodium bis(2-methoxyethoxy)aluminum hydride (120 ml), followed by reacting the mixture under reflux on heating with stirring for 15 hours, cooling the reaction mixture, pouring it in ice water (300 ml), extracting the resulting product with toluene (300 ml), three times washing with 6N-hydrochloric acid (300 ml), washing with water till the aqueous layer became neutral, drying the toluene solution over anhydrous magnesium sulfate, filtering off the drying agent, distilling off toluene, dissolving the residue in heptane, purifying according to silica gel chromatography, repeating crystallization from hexane solvent and drying to obtain the objective substance (2.1 g, 0.008 mol). This compound exhibited a CS point of -13° C., an SN point of 43° C. and an NI point of 80° C.

Workup

  1. temperatureunder reflux
  2. temperatureon heating
  3. temperaturecooling the reaction mixture
  4. extractionextracting the resulting product with toluene (300 ml), three times
  5. washwashing with 6N-hydrochloric acid (300 ml)
  6. washwashing with water till the aqueous layer
  7. dry with materialdrying the toluene solution over anhydrous magnesium sulfate
  8. filtrationfiltering off the drying agent
  9. distillationdistilling off toluene
  10. dissolutiondissolving the residue in heptane
  11. custompurifying
  12. customcrystallization from hexane solvent
  13. customdrying
  14. customto obtain the objective substance (2.1 g, 0.008 mol)
  15. customa CS point of -13° C.
  16. customan SN point of 43° C.
  17. customan NI point of 80° C.

Sources & evidence

ORD record
ord-bf9b0b5d7d794db8810f3e33eb956e21
Source dataset
uspto-grants-1993_02
Patent number
US05183587

Reaction notes

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