CCO[CH2:4][CH3:5].CN(C)P(=O)(N(C)C)N(C)C.[C:17](=[O:20])([O-])[O-:18].[K+].[K+].O([C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33]Br)C1C=CC=CC=1>O.CCCCCC>[CH:32]([CH:31]([CH:30]=[C:37]([C:5]1[CH:4]=[CH:36][CH:37]=[CH:30][CH:31]=1)[CH3:36])[C:17]([OH:18])=[O:20])([CH3:33])[CH3:35]To 2.14 g (10 mmole) of the thus-obtained acid, 10 ml ether and 10 ml hexamethylphosphorictriamide (HMPT), under nitrogen, is added 1.45 g (10.5 mmole) potassium carbonate and 2.76 g (10.5 mmole) m-phenoxybenzyl bromide. The reaction is stirred about 16 hr and then poured into hexane and water. The organic phase is washed with water, saturated sodium chloride, and dried over calcium sulfate. Solvent is removed by rotoevaporation to yield the m-phenoxybenzyl ester of 2-isopropyl-4-phenyl-3-pentenoic acid, which can be further purified by preparatory thin layer chromatography (prep. TLC) eluting with 2.5% ethyl acetate/hexane, MS m/e 400 (M30, 15), 183 (100).
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