Reaction #1914819

Reaction equation

(2,3-Dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol

NaH

butanesultone

→

4-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl-methoxy)-butane-1-sulphonic acid sodium salt

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Temperatureto reflux for 3 h
2. 2
   Otherthe solvent was removed
3. 3
   workup.ADDITIONmethanol 5 was added
4. 4
   workup.STIRRINGthe mixture was stirred
5. 5
   Filtrationfiltered
6. 6
   Concentrationthe filtrate was concentrated
7. 7
   workup.ADDITIONThe remaining oil was solidified by addition of hexane and ethanol
8. 8
   workup.STIRRINGby stirring
9. 9
   FiltrationFinal filtration
10. 10
    Otherdrying
11. 11
    Otherresulted in pure 4-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethoxy)-butane-1-sulphonic acid sodium salt

Procedure

(2,3-Dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol (6.9 g, 40 mmol) was dissolved into tetrahydrofuran (100 mL) and blanketed by nitrogen. NaH (1.76 g) was added and stirring was continued for 30 min. Then butanesultone (6.0 g) was added dropwise after which the reaction mixture was brought to reflux for 3 h. Then it was cooled to 25° C. again, the solvent was removed, methanol 5 was added, the mixture was stirred, filtered and the filtrate was concentrated. The remaining oil was solidified by addition of hexane and ethanol, followed by stirring. Final filtration and drying resulted in pure 4-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethoxy)-butane-1-sulphonic acid sodium salt as was demonstrated by NMR and mass spectroscopy.

Source