C[O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[O:19][C:18]([CH3:24])([CH3:23])[CH2:17][C:16]3([CH3:26])[CH3:25])=[CH:7][CH:6]=1.[OH-].[Na+]>CO>[CH3:23][C:18]1([CH3:24])[CH2:17][C:16]([CH3:25])([CH3:26])[C:15]2[C:20](=[CH:21][CH:22]=[C:13]([C:12]#[C:11][C:8]3[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:27])=[O:2])=[CH:10][CH:9]=3)[CH:14]=2)[O:19]1A solution of [4-(2,2,4,4-tetramethyl-chroman-6-yl-ethynyl) phenyl]acetic acid methyl ester (Compound 27, 0.047 g, 0.13 mmol) in 5 mL of methanol was treated with 1M sodium hydroxide solution (2 mL) and heated at 55° C. for 2 h. The volatiles were distilled off in vacuo and the residue was acidified with 10% hydrochloric acid and extracted with ethyl acetate (×2). The combined organic phase was washed with brine (×1), dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue which was purified by preparative reverse phase HPLC using 10% water in acetonitrile as the mobile phase to afford the title compound (0.034 g, 82%).
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