Hydrochloric Acid → HCID 178444509, compound

HRID 2301248Notes

Reaction equation

HRID 2301248 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]=[C:11]2[CH2:16][CH2:15][CH:14]([C@H:17]3[CH2:22][CH2:21][C@H:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[F:8].B1C2CCCC1CCC2.[OH-:37].[Na+].OO.Cl>C1COCC1.C1(C)C=CC=CC=1.O.C(O)C>[OH:37][CH:10]([C@H:11]1[CH2:12][CH2:13][C@H:14]([C@H:17]2[CH2:22][CH2:21][C@H:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:19][CH2:18]2)[CH2:15][CH2:16]1)[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 178444305HCID 178444305, compound

Product 1

HCID 178444509HCID 178444509, compoundYield 58%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 11.24 g (30 mmol) of 1-(3,4-difluorophenyl)-2-[4-(trans-4-pentylcyclohexyl) cyclohexylidene]ethane in 30 ml of THF were added 300 ml (150 mmol) of 0.5 M-9-BBN (THF solution) over a period of 35 minutes, at room temperature under stirring in an argon atmosphere and the mixture was stirred as such overnight. 90 ml of ethanol and 30 ml of an aqueous 6M-NaOH solution were added, and 60 ml of an aqueous 30% H2O2 solution were added over a period of 40 minutes (during this period, refluxed spontaneously). The mixture was stirred at 50° C. for 1 hr. After cooling, 180 ml of an aqueous 1M-HCl solution, water and toluene were added and the precipitate was filtered through Celite. An organic layer and an aqueous layer were separated, the aqueous layer was extracted with toluene, an extract combined with the organic layer was washed with an aqueous 5% Na2S2O3 solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the solution was condensed. The concentrate was purified by column chromatography (elution solvent: heptane:ethyl acetate=5:1). The eluate was recrystallized from 50 ml of heptane-5 ml of solmix to obtain 6.86 g of the title compound (58%, Cr 108.4-109.2 N 143.1-144.1 Iso).

Workup

  1. stirringthe mixture was stirred as such overnight
  2. temperaturerefluxed spontaneously)
  3. stirringThe mixture was stirred at 50° C. for 1 hr
  4. temperatureAfter cooling
  5. filtrationthe precipitate was filtered through Celite
  6. customAn organic layer and an aqueous layer were separated
  7. extractionthe aqueous layer was extracted with toluene
  8. washwas washed with an aqueous 5% Na2S2O3 solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off
  11. customcondensed
  12. customThe concentrate was purified by column chromatography (elution solvent: heptane:ethyl acetate=5:1)
  13. customThe eluate was recrystallized from 50 ml of heptane-5 ml of solmix

Sources & evidence

ORD record
ord-53933946430e493d8b246603659e27be
Source dataset
uspto-grants-2002_12
Patent number
US06500503B2

Reaction notes

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