Ammonium Chloride → 2-Dimethylamino-4,4-diphenyl-9-decene-5-ol

HRID 1461135Notes

Reaction equation

HRID 1461135 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[Mg].[CH3:8][N:9]([CH3:28])[CH:10]([CH3:27])[CH2:11][C:12]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:13]=[O:14].[Cl-].[NH4+]>C1COCC1>[CH3:28][N:9]([CH3:8])[CH:10]([CH2:11][C:12]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH:13]([OH:14])[CH2:6][CH2:5][CH2:4][CH:3]=[CH2:2])[CH3:27]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 707041-Pentene, 5-bromo-HCID 37771754-Dimethylamino-2,2-diphenylpentanalHCID 5462224Magnesium

Product 1

HCID 199814992-Dimethylamino-4,4-diphenyl-9-decene-5-olYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
45 °C

Procedure

A solution of 5-bromo-1-pentene (4.8 g) in anhydrous THF was added dropwise to magnesium turnings (1 g) in THF (15 ml), under nitrogen with vigorous stirring. After the initial exothermic reaction had subsided, the mixture was stirred at 45° C. for 4 hours. A solution of 4-dimethylamino-2,2-diphenylpentanal (1.2 g), as prepared above, dissolved in THF (5 ml) was then added. The resultant mixture was stirred for 18 hours. Saturated ammonium chloride solution was added and the aqueous mixture was partitioned between water and ethyl acetate (3×). The combined organic layers were washed with brine and water (once each), and dried (MgSO4). Rotary evaporation of the solution gave a crude material which was flash-chromatographed over silica gel. Elution with chloroform (CHCl3)/methanol (20:1) yielded 0.6 g of 2-dimethylamino-4,4-diphenyl-9-decene-5-ol, as a mixture of two isomers.

Workup

  1. customAfter the initial exothermic reaction
  2. additionwas then added
  3. customthe aqueous mixture was partitioned between water and ethyl acetate (3×)
  4. washThe combined organic layers were washed with brine and water (once each), and
  5. dry with materialdried (MgSO4)
  6. customRotary evaporation of the solution
  7. customgave a crude material which
  8. customwas flash-chromatographed over silica gel
  9. washElution with chloroform (CHCl3)/methanol (20:1)

Sources & evidence

ORD record
ord-4131703b7aa3491ba015a3dcadb0d43c
Source dataset
uspto-grants-1991_12
Patent number
US05073629

Reaction notes

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