[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[Li+].[CH3:13]C([N-]C(C)C)C.CCCCCCC.C(C1C=CC=CC=1)C.CI.Cl>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:13])[C:9]([OH:11])=[O:10]
To 1 g of 2-chlorophenylacetic acid, 8.8 mL of 2M LDA heptane, THF, ethylbenzene solution was dropped under cooling with ice, and further 1.58 g of HMPA and 5 mL of THF were added followed by an hour's stirring at room temperature. Then 1.25 g of methyl iodide was added under cooling with ice and stirred at room temperature for 30 minutes. The reaction solution was poured into ice water, rendered acidic with 10% aqueous hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract was dried over anhydrous magnesium sulfate and thereafter removed of the solvent by distillation under reduced pressure. The residue was purified on 30 g silica gel column chromatography (eluent, chloroform:methanol=20:1) to provide 0.928 g (yield: 86%) of the title compound as a pale yellow, oily substance.
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