[C:1]([C:5]1C=[C:7](C(=O)/C=C/C2C=CC(C(O)=O)=CC=2)[CH:8]=[C:9](C2C=CC(C)=CC=2)[C:10]=1[O:11][CH2:12][CH:13](C)C)(C)(C)[CH3:2].[OH2:36].O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH3:2][CH2:1][CH2:5][CH2:10][CH2:9][CH2:8][CH3:7].[C:10]([O:11][CH2:12][CH3:13])(=[O:36])[CH3:5]
440 mg (0.9 mmol) of 4-[(E)-3-(5-tert-butyl-6-isobutoxy-4′-methyl-3-biphenylyl)-3-oxopropenyl]benzoic acid are dissolved in 50 mL of methanol. 450 mg (1.2 mmol) of cerium chloride heptahydrate are added, and the medium is stirred for 30 minutes. 70 mg (1.9 mmol) of sodium borohydride are then added, and the reaction medium is stirred for 15 minutes until completely decolorized, and then treated with a saturated ammonium chloride solution. The residue obtained after extraction with ethyl acetate is purified by chromatography (eluent: 1 heptane/1 ethyl acetate). A white crystalline solid is obtained after recrystallization from a heptane/ethyl acetate mixture (m=180 mg; yield=42%; m.p.=175° C.).
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