Ammonia → HCID 178466082, compound

HRID 2088249Notes

Reaction equation

HRID 2088249 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]3)=[C:18]([F:29])[C:17]=2[F:30])=[C:12]([F:31])[C:11]=1[F:32])[CH3:8].C(OCC)(=O)C.N>C1COCC1>[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C@H:22]3[CH2:23][CH2:24][C@H:25]([OH:28])[CH2:26][CH2:27]3)=[C:18]([F:29])[C:17]=2[F:30])=[C:12]([F:31])[C:11]=1[F:32])[CH3:8]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 58453654HCID 58453654, compound

Product 1

HCID 178466082HCID 178466082, compoundYield 240.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (0.31 g) was suspended in THF (100 ml). 1-(4′-Ethoxy-2,2′,3,3′-tetrafluoro-1,1′-biphenyl-4-yl)-cyclohexan-4-one (s-27) (5.0 g) dissolved in THF (20 ml) was added dropwide to the suspension in the temperature range of −20° C. to −10° C., and the stirring was continued in this temperature range for another 2 hours. After the completion of the reaction had been confirmed by means of GC analysis, ethyl acetate and then a saturated aqueous solution of ammonia were added to the reaction mixture under ice-cooling and deposits were removed by filtration through Celite. The filtrate was extracted with ethyl acetate. The combined organic phase was washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by recrystallization from heptane to give trans-4-(4′-ethoxy-2,2′,3,3′-tetrafluoro-1,1′-biphenyl-4-yl)-cyclohexanol (s-28) (12.1 g). The yield based on the compound (s-27) was 89.1%.

Workup

  1. additionwas added dropwide to the suspension in the temperature range of −20° C. to −10° C.
  2. temperaturecooling
  3. customdeposits were removed by filtration through Celite
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washThe combined organic phase was washed successively with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by recrystallization from heptane

Sources & evidence

ORD record
ord-cf04f5bfe9d54fc29f6ce4fec2ef328f
Source dataset
uspto-grants-2013_05
Patent number
US08435422B2

Reaction notes

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