Diethyl Ether → 4-Dimethylamino-2,2-diphenylpentanal

HRID 1461134Notes

Reaction equation

HRID 1461134 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][N:12]([CH3:31])[CH:13]([CH3:30])[CH2:14][C:15]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:16]#N.CC[O:34]CC>C1(C)C=CC=CC=1.C1COCC1>[CH3:11][N:12]([CH3:31])[CH:13]([CH3:30])[CH2:14][C:15]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:16]=[O:34]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 31331DidiavaloHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 37771754-Dimethylamino-2,2-diphenylpentanal

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.5M diisobutylaluminum hydride in toluene (7.5 ml) was added to a stirring solution of 4-dimethylamino-2,2-diphenylpentanenitrile (3 g) in THF (7.5 ml), at -78° C. under nitrogen. The resultant mixture was then removed from the dry ice-acetone bath and allowed to warm to room temperature. Stirring was continued at room temperature for 1 day. Saturated ammonium chloride solution was added, and the resultant mixture was extracted with ethyl acetate (3×). The combined extracts were washed with brine and dried (MgSO4). An equal volume of 10% sulfuric acid was added, and the mixture was stirred at room temperature for 3 hours. Water was added, and the aqueous mixture was again extracted with ethyl acetate (3×). The combined extracts were washed with water and dried (MgSO4). Rotary evaporation of the solution gave a crude product which was treated with anhydrous ether. The separated solid material was filtered off, and the filtrate was again rotary-evaporated to yield 1.4 g of 4-dimethylamino-2,2-diphenylpentanal, as a viscous residue which solidified upon standing.

Workup

  1. customThe resultant mixture was then removed from the dry ice-acetone bath
  2. additionSaturated ammonium chloride solution was added
  3. extractionthe resultant mixture was extracted with ethyl acetate (3×)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. additionAn equal volume of 10% sulfuric acid was added
  7. stirringthe mixture was stirred at room temperature for 3 hours
  8. additionWater was added
  9. extractionthe aqueous mixture was again extracted with ethyl acetate (3×)
  10. washThe combined extracts were washed with water
  11. dry with materialdried (MgSO4)
  12. customRotary evaporation of the solution
  13. customgave a crude product which
  14. filtrationThe separated solid material was filtered off
  15. customthe filtrate was again rotary-evaporated

Sources & evidence

ORD record
ord-9a9e3879002f4669bc1645bdaec4191f
Source dataset
uspto-grants-1991_12
Patent number
US05073629

Reaction notes

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