Methanol → HCID 86666426, compound

HRID 2038813Notes

Reaction equation

HRID 2038813 reaction equation
[H-].[Na+:2].CO.[O:5]1[CH2:11][CH:10]([OH:12])[CH2:9][O:8][C:7]2=[CH:13][S:14][CH:15]=[C:6]12.[CH2:16]1[S:20](=[O:22])(=[O:21])[O:19][CH2:18][CH2:17]1>C1(C)C=CC=CC=1.CC(C)=O>[O:12]1[CH:10]([CH2:11][O:5][CH2:18][CH2:17][CH2:16][S:20]([O-:22])(=[O:21])=[O:19])[CH2:9][O:8][C:7]2=[CH:13][S:14][CH:15]=[C:6]12.[Na+:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 14264Propane sultoneHCID 24758Sodium hydrideHCID 219583633,4-Dihydro-2H-thieno[3,4-b][1,4]dioxepin-3-ol

Product 1

HCID 86666426HCID 86666426, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent3×

Conditions

Temperature
40 °C

Procedure

The monomer was formed as follows. Initially, 5.86 grams of pure NaH and 240 milliliters of toluene were added to three necks of a round bottom flask equipped with a stirrer, thermometer, and condenser placed in a heating mantle. The mixture was kept under argon. A solution of 40 grams 2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol (EDOT MeOH) and 3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin-3-ol (ProDOT-OH) (ratio 80:20) in 400 ml toluene were added drop wise for 15 minutes. The mixture was stirred at 40° C. for 1 hour. A solution of 28.4 grams of propane sultone in 240 milliliters toluene was added drop wise during 15 minutes. The resulting mixture was heated at reflux for an additional 2 hours. The solution was cooled to ambient temperature and 3.6 liters of acetone was added quickly. The precipitated product was filtered through a fine porosity frit and then dried under vacuum at ambient temperature for 6 days. 61 grams of sodium 3-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2-ylmethoxy)-propane-1-sulfonate (EDOTSNa) was obtained (83% yield).

Workup

  1. customThe monomer was formed
  2. customequipped with a stirrer
  3. customthermometer, and condenser placed in a heating mantle
  4. temperatureThe resulting mixture was heated
  5. temperatureat reflux for an additional 2 hours
  6. temperatureThe solution was cooled to ambient temperature
  7. filtrationThe precipitated product was filtered through a fine porosity frit
  8. customdried under vacuum at ambient temperature for 6 days

Sources & evidence

ORD record
ord-43b8bad7d1f44bd192c7150cbc5c2680
Source dataset
uspto-grants-2013_11
Patent number
US08576543B2

Reaction notes

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