O1CCC[CH2:2]1.[C:6]([O:17]C)(=O)[C:7]1[CH:15]=[C:13]([OH:14])[C:11]([OH:12])=[C:9]([OH:10])[CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O>C(OCC)(=O)C.O>[OH:10][C:9]1[CH:8]=[C:7]([CH:15]=[C:13]([OH:14])[C:11]=1[O:12][CH3:2])[CH2:6][OH:17]
Next, a tetrahydrofuran solution (4 mL) with 4-methoxy form (560 mg, 2.8 mmol) with methyl gallate was dropped carefully to a tetrahydrofuran (THF) solution (6 mL) with lithium aluminum hydride (469 mg, 12.4 mmol) in an ice bath (0° C.). Then, the mixture was stirred for six hours at 60 to 65° C., ethyl acetate and a 10% sulfuric acid aqueous solution were added to the mixture, and then the reaction was stopped. Purified water was added to the reaction liquid, extraction was performed with the ethyl acetate, and the separated ethyl acetate layer was washed with saturated saline and dehydrated by sodium sulfate. After concentration, the extract liquid was purified by silica gel column chromatography (solvent: chloroform-methanol (50:1, v/v)→chloroform-methanol (50:3 , v/v)) and a reductant, that is, synthetic 3,5-dihydroxy-4-methoxybenzyl alcohol of 175.9 mg (yield: 36.6%) was obtained.
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