1,4-Butane sultone → Sodium 4-((2,3-dihydrothieno(3,4-b)(1,4)dioxin-2-yl)methoxy)butane-1-sulfonate

HRID 1825692Notes

Reaction equation

[O:1]1[CH:6]([CH2:7][OH:8])[CH2:5][O:4][C:3]2=[CH:9][S:10][CH:11]=[C:2]12.[H-].[Na+:13].[CH2:14]1[S:19](=[O:21])(=[O:20])[O:18][CH2:17][CH2:16][CH2:15]1>O1CCCC1>[Na+:13].[O:1]1[CH:6]([CH2:7][O:8][CH2:17][CH2:16][CH2:15][CH2:14][S:19]([O-:21])(=[O:20])=[O:18])[CH2:5][O:4][C:3]2=[CH:9][S:10][CH:11]=[C:2]12

Participants

Conditions

Temperature: 25 °C

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. Sodium hydride (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 was added, the mixture was stirred, filtered and the filtrate was concentrated. The remaining oil was solidified by addition of hexanes 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-sulfonic acid sodium salt as was demonstrated by NMR and mass spectroscopy.

Workup

temperatureto reflux for 3 h
customthe solvent was removed
additionmethanol was added
stirringthe mixture was stirred
filtrationfiltered
concentrationthe filtrate was concentrated
additionThe remaining oil was solidified by addition of hexanes and ethanol
stirringby stirring
filtrationFinal filtration
customdrying
customresulted in pure 4-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethoxy)-butane-1-sulfonic acid sodium salt

Sources & evidence

ORD record: ord-b69d140b944a43d4b44f3e9b33fc5b6b
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07048874B2

Reaction notes

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