Dimethyl Sulfoxide → HCID 69553893, compound

HRID 1744719Notes

Reaction equation

HRID 1744719 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][OH:8])[CH2:2][CH2:3][CH3:4].CS(C)=O.[H-].[Na+].S(OCC1CCC=CC1)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=O)=O>O>[CH2:1]([O:5][CH2:6][CH2:7][O:8][CH2:22][CH:21]1[CH2:23][CH2:24][CH2:18][CH:19]=[CH:20]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81332-ButoxyethanolHCID 24758Sodium hydrideHCID 11459813HCID 11459813, compound

Product 1

HCID 69553893HCID 69553893, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 niL round bottom flask equipped with a mechanical stirrer was charged with 16.7g (0.15 mol) 2-butoxyethanol, and 150 mL of DMSO. Sodium hydride (4.22 g, 95% in purity; 0.167 mol) was slowly added to above mixture in an ice bath over 20 min. After the above mixture was reacted at room temperature for 3 hrs, 39.9 g (0.15 mol) of 3-cyclohexene-1-methanol tosylate was slowly added to the above mixture over 20 min. The reaction was carried at room temperature overnight, then 80° C. for 3 hrs. The reaction mixture was added to water (150 mL), and then extracted with chloroform (3×150 mL), washed with water (2×100 mL), dried with sodium sulfate. The solvent was evaporated and the residue distilled to give pure product.

Workup

  1. customA 500 niL round bottom flask equipped with a mechanical stirrer
  2. customAfter the above mixture was reacted at room temperature for 3 hrs
  3. wait80° C. for 3 hrs
  4. extractionextracted with chloroform (3×150 mL)
  5. washwashed with water (2×100 mL)
  6. dry with materialdried with sodium sulfate
  7. customThe solvent was evaporated
  8. distillationthe residue distilled
  9. customto give pure product

Sources & evidence

ORD record
ord-d23013df59de49af9b445b9623b42ec1
Source dataset
uspto-grants-2006_03
Patent number
US07018559B2

Reaction notes

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