P(CCCC)(CCCC)CCCC.CCN(CC)CC.[CH2:21]([OH:26])[CH:22]([OH:25])[CH:23]=[CH2:24].Br[C:28]1[CH:29]=[C:30]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:31]=[CH:32][CH:33]=1>CN(C=O)C.O>[OH:26][CH2:21][C:22](=[O:25])[CH2:23][CH2:24][C:32]1[CH:31]=[C:30]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:29]=[CH:28][CH:33]=1
To a stirred solution of Pd (OAc)2 (75 mg, 0.34 mmol), nBu3P (136 mg, 0.67 mmol), and Et3N (442 mg, 4.37 mmol) in DMF (10 ml) was added 3-butene-1,2-diol (296 mg, 3.36 mmol) followed by methyl 3-bromophenylacetate (1.0 g, 4.37 mmol), and the reaction mixture was stirred at 100° C. for 5 h. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried (magnesium sulfate) and evaporated in vacuo. The residue was purified by silica gel (25 g) column chromatography eluting with toluene/ethyl acetate (20:1) to give methyl 3-(4-hydroxy-3-oxobutyl)phenylacetate (193 mg, 24.4%) as an oil.
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