Dimethyl Sulfide → 2-Dimethylamino-4,4-diphenyl-5-oxononanal

HRID 1461137Notes

Reaction equation

FC(F)(F)C(O)=[O:4].[CH3:8][N:9]([CH3:33])[CH:10]([CH2:12][C:13]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:14](=[O:20])[CH2:15][CH2:16][CH2:17][CH:18]=C)[CH3:11].O=[O+][O-].CSC>CO>[CH3:8][N:9]([CH3:33])[CH:10]([CH2:12][C:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:14](=[O:20])[CH2:15][CH2:16][CH2:17][CH3:18])[CH:11]=[O:4]

Participants

Conditions

Temperature: -20 °C

Procedure

Trifluoroacetic acid (1 ml) was added to a solution of 2-dimethylamino-4,4-diphenyl-9-decene-5-one (270 mg) in methanol (5 ml) to adjust the pH to 2.0. The solution was rotary evaporated, and the residue was taken up in methanol. A gentle stream of ozone was passed through the solution at -78° C., until the color turned to sky blue. The reaction was warmed to -20° C., and dimethyl sulfide (3 ml) was added. Rotary evaporation of the solution gave a crude material which was flash-chromatographed over silica gel. Elution with chloroform/methanol (30:1) yielded 80 mg of 2-dimethylamino-4,4-diphenyl-5-oxo-nonanal.

Workup

customwas passed through the solution at -78° C., until the color
customRotary evaporation of the solution
customgave a crude material which
customwas flash-chromatographed over silica gel
washElution with chloroform/methanol (30:1)

Sources & evidence

ORD record: ord-69385108eebc4329944a1d20538d75c4
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05073629

Reaction notes

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