[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].N1CCOCC1.N1C=CC=CC=1.[CH2:20]([CH:22]([CH2:25][CH:26]=[CH2:27])C=O)[CH3:21].Cl>C1(C)C=CC=CC=1.C(O)(=O)CC(O)=O.O.C(#N)C>[CH2:26]([CH:25]([CH2:22][CH:20]=[CH2:21])/[CH:1]=[CH:2]/[C:3]([OH:5])=[O:4])[CH3:27]Malonic acid (93.74 g, 0.90 mol), acetonitrile (306 mL), morpholine (26 mL, 0.30 mol), and pyridine (97 mL, 1.20 mol) were added in this order to the solution of 2-ethylpent-4-enal (58.44 g) in toluene obtained by the method described above under a nitrogen atmosphere, and the mixture was slowly warmed to approximately 80° C. over approximately 1 hour. After stirring at approximately 80° C. for 13.5 hours, malonic acid (6.24 g, 0.06 mol) was added thereto, and the mixture was further stirred at approximately 80° C. for 3 hours and cooled to room temperature. To the reaction mixture, water (408 mL) was added, and concentrated hydrochloric acid (130 mL) was added to separate an organic layer. The aqueous layer was subjected to extraction with toluene (153 mL), and the extract was combined with the organic layer, followed by two extractions of the compound of interest into aqueous layers using a 2 M aqueous NaOH solution (360 mL×1 and 90 mL×1). The aqueous layers were combined and then adjusted to be acidic by the addition of concentrated hydrochloric acid (80 mL), followed by two extractions with toluene (each with 204 mL). The organic layers were combined and then washed with water (102 mL). The organic layer was concentrated under reduced pressure to obtain the title compound (100.57 g, yellow oil substance).
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