2-Methoxyethanol → HCID 66857574, compound

HRID 252272Notes

Reaction equation

HRID 252272 reaction equation
[CH3:1][O:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:9][O:10][CH2:11]CO.S([O-])(O)(=O)=O.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:9][O:10][CH2:11][CH2:1][O:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 80192-MethoxyethanolHCID 141826Thiophene, 2-methoxy-3-methyl-HCID 516919Sodium Bisulfate

Product 1

HCID 66857574HCID 66857574, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-methoxy-3-methyl-thiophene, (1.5 g, 11.7 mmol) 2-methoxy-ethanol (3.8 g, 50.5 mmol, 4.3 equiv.) and sodium hydrogen sulfate anhydrous (100 mg, 0.833 mmol, 0.07 equiv.) were stirred in toluene at 120° C. for 3.5 hours. The mixture was diluted with ethyl acetate and extracted with sodium bicarbonate solution. The organic solvent washed with brine, dried over magnesium sulfate dihydrate, filtered and evaporated. After Kugelrohr distillation, 980 mg of the title compound were obtained as a light yellow oil GC-MS (EI) M=172.

Workup

  1. extractionextracted with sodium bicarbonate solution
  2. washThe organic solvent washed with brine
  3. dry with materialdried over magnesium sulfate dihydrate
  4. filtrationfiltered
  5. customevaporated
  6. distillationAfter Kugelrohr distillation

Sources & evidence

ORD record
ord-5a1c3d61cfdb48c4abdfef852f2b82e9
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

Loading…