Hydrochloric Acid → HCID 178419208, compound

HRID 720769Notes

Reaction equation

HRID 720769 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-:5].[Na+].[C:7]([C:11]1[CH:12]=[C:13]([PH:23](=O)[C:24]2[CH:29]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:27]([O:34][CH3:35])=[C:26]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:25]=2)[CH:14]=[C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]=1[O:17][CH3:18])([CH3:10])([CH3:9])[CH3:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1.C1(C)C=CC=CC=1.O>[C:30]([C:28]1[CH:29]=[C:24]([PH:23][C:13]2[CH:12]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:16]([O:17][CH3:18])=[C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:14]=2)[CH:25]=[C:26]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:27]=1[O:34][CH3:35])([CH3:31])([CH3:32])[CH3:33].[BH3:5]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 21226445Aluminium lithium hydrideHCID 178490127HCID 178490127, compound

Product 1

HCID 178419208HCID 178419208, compoundYield 39.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under argon atmosphere, a solution of cerium chloride (4.55 g, 3.0 equivalents) in THF (25 mL) was stirred at room temperature (25° C.) for 30 minutes. After sodium borohydride (0.72 g, 3.1 equivalents) was added, the mixture was stirred at room temperature for 1 hour. Then, bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine oxide (3.0 g, 6.16 mmol) synthesized in Reference Example 3 and lithium aluminum hydride (0.28 g, 1.2 equivalents) were successively added at 5° C., and the mixture was stirred at room temperature for 18 hours. After water (10 mL) was added at 3° C. and toluene (30 mL) and 6M-HCl (20 mL) were then added, the mixture was stirred at room temperature for 30 minutes. The reaction solution was allowed to separate into layers. An aqueous layer was extracted with toluene (30 mL). Organic layers were combined, washed with a 5% NaCl aqueous solution (20 mL), dried over anhydrous magnesium sulfate and then naturally filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (alumina 25 g, n-hexane). The residue was recrystallized from heptane to obtain the title compound (1.18 g, white crystal). Yield 39.6%, mp. 134.7° C.

Workup

  1. additionwere successively added at 5° C.
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. customto separate into layers
  5. extractionAn aqueous layer was extracted with toluene (30 mL)
  6. washwashed with a 5% NaCl aqueous solution (20 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationnaturally filtered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by column chromatography (alumina 25 g, n-hexane)
  11. customThe residue was recrystallized from heptane

Sources & evidence

ORD record
ord-ff84fc9c43e9432783a18a5bbb04d877
Source dataset
uspto-grants-2006_11
Patent number
US07135582B2

Reaction notes

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