[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(N(CC)CC)C.C(O)(=O)[CH2:26][C:27]([OH:29])=[O:28].P([O-])(O)(O)=O.[Na+]>C1(C)C=CC=CC=1.CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]/[CH2:26][C:27]([OH:29])=[O:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]Under a nitrogen atmosphere, 8-heptyloxy-octanal (178.0 mg, 0.734 mmol) obtained in Step D-2 was dissolved in toluene (3.56 mL), and triethylamine (184 μL, 1.32 mmol) and a solution of malonic acid (137.6 mg, 1.32 mmol) in DMF (0.178 mL) were added in order at 75° C. The mixture was stirred at 90° C. for 16 hours. After cooling to room temperature, an aqueous solution (2.6 mL) of 30% sodium dihydrogen phosphate and ethyl acetate (5.2 mL) were added, and the mixture was stirred at room temperature for 5 minutes. After extraction, the organic layer was washed with water. The aqueous layer was washed with ethyl acetate. The combined organic layer was then washed again with water and a saturated brine, dried over anhydrous sodium sulfate, and then filtered. The solvent was distilled off to obtain 209.7 mg (quant.) of (E)-10-heptyloxy-dec-3-enoic acid (ESI (LC/MS positive mode) m/z 285 (M+H); Rt 2.23 min.)
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