Water → 1-(9,10-Dihydroxyoctadecyl)-3,7-dimethylxanthine

HRID 1870854Notes

Reaction equation

HRID 1870854 reaction equation
[CH2:1]([N:19]1[C:28](=[O:29])[C:27]2[N:26]([CH3:30])[CH:25]=[N:24][C:23]=2[N:22]([CH3:31])[C:20]1=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C[N+]1([O-])CC[O:36]CC1.S([O-])([O-])=O.[Na+].[Na+].[OH2:46]>CC(C)=O>[OH:46][CH:9]([CH:10]([OH:36])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:19]1[C:28](=[O:29])[C:27]2[N:26]([CH3:30])[CH:25]=[N:24][C:23]=2[N:22]([CH3:31])[C:20]1=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 537845551-(9-Octadecenyl)-3,7-dimethylxanthine

Product 1

HCID 234356351-(9,10-Dihydroxyoctadecyl)-3,7-dimethylxanthineYield 40.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1-(9-octadecenyl)-3,7-dimethylxanthine (0.15 g, 0.35 mmol), 4-methylmorpholine-N-oxide (49 mg, 0.42 mmol, 1.2 equivalents.) and potassium osmate dihydrate (1 mg) in acetone (4 ml) and water (1 ml) was stirred for 6 hours. A solution of 20% aqueous sodium sulphite (2 ml) was added and stirred for 30 minutes. The reaction mixture was extracted with four 10 ml aliquots of 25% ethanol/dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate, the solvent evaporated under reduced pressure and a residue purified by flash chromatography over silica gel using a methanol(5%)/dichloromethane eluant, yielding 0.65 g of 1-(9,10-dihydroxyoctadecyl)-3,7-dimethylxanthine (40.4% yield).

Workup

  1. extractionThe reaction mixture was extracted with four 10 ml aliquots of 25% ethanol/dichloromethane
  2. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  3. customthe solvent evaporated under reduced pressure
  4. customa residue purified by flash chromatography over silica gel using a methanol(5%)/dichloromethane eluant

Sources & evidence

ORD record
ord-eff17d1969c94dc2b1f9579476832299
Source dataset
uspto-grants-2000_08
Patent number
US06100271

Reaction notes

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