Acetone → HCID 15885495, compound

HRID 1870856Notes

Reaction equation

HRID 1870856 reaction equation
[CH2:1]([N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH3:23])[CH:18]=[N:17][C:16]=2[N:15]([CH3:24])[C:13]1=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]CC=C.C[N+]1([O-])CC[O:29]CC1.S([O-])([O-])=O.[Na+].[Na+].[CH3:39][C:40]([CH3:42])=[O:41]>O>[OH:41][CH:40]([CH2:42][OH:29])[CH2:39][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH3:23])[CH:18]=[N:17][C:16]=2[N:15]([CH3:24])[C:13]1=[O:14]

Participants

6

Reactant 4

HCID 180AcetoneHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 158854941-(10-Undecenyl)-3,7-dimethylxanthine

Product 1

HCID 15885495HCID 15885495, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-(10-undecenyl)-3,7-dimethylxanthine (4.3 g, 13 mmol), prepared above, 4-methylmorpholine-N-oxide (1.942 g, 16.6 mmol) and potassium osmate dihydrate (9.5 mg, 0.026 mmol) in acetone (45 ml) and water (10 ml) was stirred for 6 hours. A solution of 20% aqueous sodium sulphite (12 ml) was added and stirred for 30 minutes. The reaction mixture was extracted with four 100 ml aliquots of 25% ethanol/dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate. Evaporating the solvent under reduced pressure left a residue, which upon subsequent purification by flash chromatography over silica gel using a methanol (5%)/dichloromethane eluant produced 3.6 g of 1-(10,11-dihydroxyundecanyl)-3,7-dimethylxanthine (76% yield).

Workup

  1. stirringstirred for 30 minutes
  2. extractionThe reaction mixture was extracted with four 100 ml aliquots of 25% ethanol/dichloromethane
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. customEvaporating the solvent under reduced pressure
  5. waitleft a residue, which
  6. customupon subsequent purification by flash chromatography over silica gel using a methanol (5%)/dichloromethane eluant

Sources & evidence

ORD record
ord-f965a5f7bd3a406bb25fa2c6be33a01e
Source dataset
uspto-grants-2000_08
Patent number
US06100271

Reaction notes

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