[H-].[Na+].[NH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.[C:14]1([CH2:20][CH2:21][CH2:22][CH2:23]CO)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:26]O>C1(C)C=CC=CC=1>[CH3:26][CH:22]([CH2:21][CH2:20][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:23][CH2:11][O:10][C:8](=[O:9])[C:7]1[CH:6]=[CH:5][C:4]([NH2:3])=[CH:13][CH:12]=1Sodium hydride (600 mg, cat. 60% disp in oil) was added to a suspension of methyl 4-aminobenzoate (30 g, 19 mmol), 3-methyl, 5-phenyl pentanol (36 g, 20 mmol) in PhMe (100 mL). The suspension was heated under reflux for 24 hours with the azeotropic removal of MeOH. The mixture was cooled and filtered through a plug of silica (400 mL) with cyclohexane:isopropanol (95:5) as eluant to give the ester as a pale yellow oil (15 g, 25%) which slowly crystallized.
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