Hydrochloric Acid → HCID 178419139, compound

HRID 1272611Notes

Reaction equation

HRID 1272611 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-:5].[Na+].[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[PH:17](=O)[C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1.C1(C)C=CC=CC=1>[CH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[PH:17][C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1.[BH3:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 21226445Aluminium lithium hydrideHCID 178527025HCID 178527025, compound

Product 1

HCID 178419139HCID 178419139, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, a solution of cerium chloride (8.66 g, 3.0 equivalents) in THF (80 mL) was stirred at room temperature (25° C.) for 30 min. Sodium borohydride (1.37 g, 3.1 equivalents) was added, and the mixture was stirred at room temperature for 1 hr. Then bis(2-naphthyl)phosphine oxide (3.54 g, 0.012 moL) synthesized in Reference Example 12 and lithium aluminum hydride (0.53 g, 1.2 equivalents) were successively added at 5° C. and the mixture was stirred at room temperature for 3 hrs. Toluene (80 mL) was added at 0° C. and then 3M-HCl (30 mL) was added. The mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned, and the aqueous layer was extracted with toluene (40 mL). The combined organic layer was washed with 5% aqueous NaCl solution (20 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and the filtrate was concentrated under reduced pressure. Toluene (30 mL) and silica gel (10 g) were added to the residue and the mixture was stirred at room temperature for 10 min. The mixture was filtered by gravity, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from heptane to give the title compound (2.23 g, white crystals). yield 63.3%. melting point: 113.2° C.

Workup

  1. additionwere successively added at 5° C.
  2. stirringthe mixture was stirred at room temperature for 3 hrs
  3. stirringThe mixture was stirred at room temperature for 30 min
  4. customThe reaction mixture was partitioned
  5. extractionthe aqueous layer was extracted with toluene (40 mL)
  6. washThe combined organic layer was washed with 5% aqueous NaCl solution (20 mL)
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered by gravity
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. additionToluene (30 mL) and silica gel (10 g) were added to the residue
  11. stirringthe mixture was stirred at room temperature for 10 min
  12. filtrationThe mixture was filtered by gravity
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. customThe residue was recrystallized from heptane

Sources & evidence

ORD record
ord-704afbb7d23d40169fa1d2323391de15
Source dataset
uspto-grants-2007_04
Patent number
US07208633B2

Reaction notes

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