Hydrochloric Acid → HCID 178419165, compound

HRID 1272603Notes

Reaction equation

HRID 1272603 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-:5].[Na+].[CH3:7][C:8]1[CH:9]=[C:10]([PH:15](=O)[C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=2)[CH:11]=[C:12]([CH3:14])[CH:13]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1.C1(C)C=CC=CC=1.O>[CH3:23][C:18]1[CH:17]=[C:16]([PH:15][C:10]2[CH:9]=[C:8]([CH3:7])[CH:13]=[C:12]([CH3:14])[CH:11]=2)[CH:21]=[C:20]([CH3:22])[CH:19]=1.[BH3:5]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 21226445Aluminium lithium hydrideHCID 178425332HCID 178425332, compound

Product 1

HCID 178419165HCID 178419165, compoundYield 70.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen stream, a solution of cerium chloride (2.87 g, 2.99 equivalents) in THF (20 mL) was stirred at room temperature (25° C.) for 40 min. Sodium borohydride (0.44 g, 10, 2.99 equivalents) was added, and the mixture was stirred at room temperature for 1 hr. Bis(3,5-dimethylphenyl)phosphine oxide (1.00 g, 3.89 mmol) synthesized in Reference Example 2 and lithium aluminum hydride (0.17 g, 1.16 equivalents) were successively added at −12° C. The mixture was stirred for 4 hrs. Water (10 mL) and then toluene (20 mL) were added at −10° C., and 6M-HCl (3 mL) was added at −5° C. The mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned, and the organic layer was concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (10 g, toluene) and an effective fraction was concentrated under reduced pressure. The residue was recrystallized from heptane to give the title compound (0.70 g, white powder). yield 70.6%. melting point: 106.5° C.

Workup

  1. additionwere successively added at −12° C
  2. stirringThe mixture was stirred for 4 hrs
  3. stirringThe mixture was stirred at room temperature for 30 min
  4. customThe reaction mixture was partitioned
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe concentrate was purified by silica gel column chromatography (10 g, toluene)
  7. concentrationan effective fraction was concentrated under reduced pressure
  8. customThe residue was recrystallized from heptane

Sources & evidence

ORD record
ord-1557707cf6a74d898e4742971e9dc0e9
Source dataset
uspto-grants-2007_04
Patent number
US07208633B2

Reaction notes

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