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

HRID 2223988Notes

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-49857b7065f04e469985b4f588d9ad32
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378039B2

Reaction notes

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