tert-Butanol → 3-(5,6-Dihydroxyhexyl)-1-methyluracil

HRID 361517Notes

Reaction equation

HRID 361517 reaction equation
[CH2:1]([N:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([CH3:14])[C:8]1=[O:15])[CH2:2][CH2:3]CC=C.C[N+]1([O-])CC[O:20]CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:32]([OH:36])(C)([CH3:34])[CH3:33]>[Os](=O)(=O)(=O)=O.CC(C)=O.O>[OH:36][CH:32]([CH2:34][OH:20])[CH2:33][CH2:3][CH2:2][CH2:1][N:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([CH3:14])[C:8]1=[O:15]

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 232958743-(5-Hexenyl)-1-methyluracil

Product 1

HCID 232879503-(5,6-Dihydroxyhexyl)-1-methyluracilYield 66%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution of 3-(5-hexenyl)-1-methyluracil (598 mg, 2.9 mmol), 4-methylmorpholine-N oxide (408 mg, 3.5 mmol), and a 2.5% solution in t-butanol of osmium tetroxide (3 drops) in acetone (15 mL) and water (5 mL) was stirred for 3 days. After addition of a saturated solution of sodium hydrosulfite (10 mL) and 15 minutes, the reaction mixture was added to water (15 mL) and extracted with 20% ethanol/dichloromethane (4×40 mL). The combined organic layers were dried over sodium sulfate and the solvent is evaporated under vacuum to give 461 mg (66%) 3-(5,6-dihydroxyhexyl)-1-methyluracil (inventive compound no. 1811) as a colorless oil.

Workup

  1. extractionextracted with 20% ethanol/dichloromethane (4×40 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-e4cc6d9d460442bfb93016cb31699534
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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