[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH2:2]1.C([Li])CCC.[C:15](=[O:17])=[O:16].C([O-])(O)=O.[Na+]>CCOCC.CCCCCC>[CH2:2]1[O:3][C:4]2[C:5](=[C:6]([C:15]([OH:17])=[O:16])[CH:7]=[CH:8][CH:9]=2)[O:1]1A solution of 1,3-benzodioxole (3.09 g, 32 mmol) in dry ether (50 mL) was treated dropwise at −10° C. with 2.5 M n-butyllithium (15 mL, 35 mmol) in hexane. When the addition was complete, the mixture was stirred under reflux for one hour. After cooling to room temperature, it was added to crushed solid carbon dioxide, and after 24 hours, the residue was treated with 10% aq. NaHCO3 and ether. The alkali layer was separated, washed with ether, then acidified with cold concentrated HCl, and extracted with chloroform. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure (1.1 g, 20%). EI-MS m/z 167 (M+H)+.
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