Dimethyl Sulfoxide → HCID 58662607, compound

HRID 1181591Notes

Reaction equation

HRID 1181591 reaction equation
[CH:1]1([CH:4]([CH:6]2[CH2:8][CH2:7]2)[OH:5])[CH2:3][CH2:2]1.S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:13][C@@H:14]1[O:16][CH2:15]1)(=O)=O.[H-].[Na+].CS(C)=O>O1CCCC1.O>[CH:1]1([CH:4]([CH:6]2[CH2:8][CH2:7]2)[O:5][CH2:13][C@H:14]2[CH2:15][O:16]2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 84336DicyclopropylmethanolHCID 14292098(R)-(-)-Glycidyl-4-nitrobenzenesulfonate

Product 1

HCID 58662607HCID 58662607, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dicyclopropylmethanol (880 mg) obtained in Step 1 and (R)-glycidyl nosylate (3.05 g) were dissolved in tetrahydrofuran (7.3 ml), sodium hydride (471 mg) and dimethyl sulfoxide (1.5 ml) were added under ice-cooling, and the mixture was stirred at room temperature for 5 hr. Water was poured into the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10) to give the title compound (760 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed successively with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10)

Sources & evidence

ORD record
ord-2eb94568e98f4ca79d5d6e44134dc735
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

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