Benzenesulfinic acid, sodium salt → 6-Benzenesulfonyl-hexa-2,4-dienoic acid methyl ester

Temperature

20 °C

A mixture of 6-bromohexa-2,4-dienoic acid methyl ester (0.41 g, 2.0 mmol), sodium benzene sulfinate (0.33 g, 2.0 mmol) and tetra-n-butylammonium iodide (37 mg, 0.1 mmol) was heated at reflux in dry THF (10 mL) under an atmosphere of nitrogen for 2 hours. The resulting slurry was allowed to cool to 20° C. and filtered. The filtrate was concentrated under reduced pressure to give an oil that was dissolved in ethyl acetate (20 mL). This solution was washed successively with saturated aqueous sodium hydrogen carbonate (10 mL), distilled water (10 mL), then with brine (10 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an oil that was purified by flash chromatography (7:3 to 1:1 to 1:1 60-80° C. petroleum ether:diethyl ether) to give a solid that was recrystallised to give the title compound (0.39 g, 73%) as white crystals, mp 105° C.

1. temperaturewas heated
2. filtrationfiltered
3. concentrationThe filtrate was concentrated under reduced pressure
4. customto give an oil that
5. washThis solution was washed successively with saturated aqueous sodium hydrogen carbonate (10 mL)
6. distillationdistilled water (10 mL)
7. dry with materialThe organic layer was dried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto give an oil that
11. customwas purified by flash chromatography (7:3 to 1:1 to 1:1 60-80° C. petroleum ether:diethyl ether)
12. customto give a solid
13. customthat was recrystallised

ORD record

ord-dc0952acbd134df5b69bf358f0fc070e

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683185B2