[OH:1][C:2]1[C:7]([OH:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].Br[CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[CH:15]1([O:8][C:7]2[C:2]([OH:1])=[C:3]([C:11](=[O:13])[CH3:12])[CH:4]=[CH:5][C:6]=2[O:9][CH3:10])[CH2:19][CH2:18][CH2:17][CH2:16]1A mixture of 1-(2,3-dihydroxy-4-methoxyphenyl)ethanone (10 g, 55 mmol), bromocyclopentane (6.0 mL, 56 mmol), potassium carbonate (15.5 g, 112 mmol), and anhydrous DMF (100 mL) was heated at 110° C. under N2 for 17 h and then allowed to cool to rt. The mixture was poured into 0.5N HCl (600 mL) and extracted with diethyl ether (250 mL×2). The combined extracts were dried, filtered, concentrated, and purified by silica gel chromatography (1:0→17:3; hexanes:ethyl acetate) to give 1-[3-(cyclopentyloxy)-2-hydroxy-4-methoxyphenyl]ethanone: MS (ESI): 251.2.
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