Dimethyl Sulfoxide → 2-Dimethylamino-4,4-diphenyl-9-decene-5-one

HRID 1461136Notes

Reaction equation

HRID 1461136 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][N:12]([CH3:36])[CH:13]([CH2:15][C:16]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:17]([OH:23])[CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])[CH3:14]>C(Cl)Cl.O>[CH3:36][N:12]([CH3:11])[CH:13]([CH2:15][C:16]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])[CH3:14]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 199814992-Dimethylamino-4,4-diphenyl-9-decene-5-ol

Product 1

HCID 199815122-Dimethylamino-4,4-diphenyl-9-decene-5-oneYield 50.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Anhydrous dimethyl sulfoxide (DMSO, 8.8 ml) was carefully added by syringe to a stirred solution of oxalyl chloride (4.8 ml) in methylene chloride (40 ml), maintained at -50° C. to -60° C. The mixture was then stirred 2 min. A solution of 2-dimethylamino-4,4-diphenyl-9-decene-5-ol (1 g) in methylene chloride (2 ml) was added, and stirring continued for 5 min. The mixture was allowed to warm to room temperature, diluted with water, and washed with sodium bicarbonate solution. Rotary evaporation of the solution gave a crude product which was flash-chromatographed over silica gel. Elution with chloroform/methanol (20:1) yielded 0.5 g of 2-dimethylamino-4,4-diphenyl-9-decene-5-one.

Workup

  1. temperaturemaintained at -50° C. to -60° C
  2. stirringstirring
  3. waitcontinued for 5 min
  4. washwashed with sodium bicarbonate solution
  5. customRotary evaporation of the solution
  6. customgave a crude product which
  7. customwas flash-chromatographed over silica gel
  8. washElution with chloroform/methanol (20:1)

Sources & evidence

ORD record
ord-df6d85474049489a85c825d1926207eb
Source dataset
uspto-grants-1991_12
Patent number
US05073629

Reaction notes

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