Reaction SMILES: O1CCCCC1OC1CCCCO1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20](O)[C:21]2[CH:26]=[CH:25][C:24](/[CH:27]=[C:28](\[CH3:34])/[CH2:29][O:30][CH2:31][CH2:32][OH:33])=[CH:23][CH:22]=2)[CH:15]=1.S(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl.C(OCC)(=O)C.O.C(O)(=O)C.[Zn].N1C=CC=CC=1>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21]2[CH:26]=[CH:25][C:24](/[CH:27]=[C:28](\[CH3:34])/[CH2:29][O:30][CH2:31][CH2:32][OH:33])=[CH:23][CH:22]=2)[CH:15]=1
Reactant: C/C(=C\c1ccc(C(O)c2cccnc2)cc1)COCCO
Agent: C1CCC(OC2CCCCO2)OC1
Agent: O=C([O-])O
Agent: [Na+]
Solvent: ClCCl
Solvent: O
Solvent: O=S(Cl)Cl
Product: C/C(=C\c1ccc(Cc2cccnc2)cc1)COCCO

Procedure:
In 5 ml of methylene chloride was dissolved 180 mg of tetrahydropyranyl ether of 2-[(E)-3-[4-(pyridin-3-yl-hydroxymethyl)phenyl]-2-methylallyloxy]ethanol, and 0.08 ml of pyridine was added to the resulting solution, after which 0.12 ml of thionyl chloride was further added thereto. The resulting mixture was subjected to reaction under reflux for 2 hours. The excessive thionyl chloride and the solvent were removed by distillation under reduced pressure, and the residue thus obtained was dissolved in a mixed solvent of 20 ml of ethyl acetate and 20 ml of water, after which the pH of the resulting solution was adjusted to 7.5 with a saturated aqueous sodium hydrogencarbonate solution. Subsequently, the organic layer was separated, washed successively with 20 ml of water and 20 ml of a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure, to obtain crude tetrahydropyranyl ether of 2-[(E)-3-[4-pyridin-3-ylchloromethyl)phenyl]-2-methylallyloxy]ethanol. This was dissolved in 2 ml of acetic acid, and 62 mg of zinc powder was added to the resulting solution at room temperature, after which the resulting mixture was subjected to reaction at the same temperature for one hour. Subsequently, 30 ml of ethyl acetate and 20 ml of water were added to the reaction mixture, and the pH thereof was adjusted to 7.5 with sodium hydrogencarbonate, after which the organic layer was separated. This organic layer was successively washed with 20 ml of water and 20 ml of a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure to obtain crude tetrahydropyranyl ether of 2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]ethanol. This was dissolved in 5 ml of ethanol, and 180 mg of p-toluenesulfonic acid monohydrate was added to the resulting solution at room temperature, after which the resulting mixture was subjected to reaction at the same temperature for one hour. Subsequently, the solvent was removed by distillation under reduced pressure, and 20 ml of ethyl acetate and 20 ml of water were added to the residue thus obtained, after which the pH thereof was adjusted to 7.5 with sodium hydrogencarbonate. The organic layer was then separated, washed successively with 20 ml of water and 20 ml of a saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: toluene:ethyl acetate (1:1 by volume)] to obtain 50 mg (yield 37.6 %) of colorless, oily 2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]ethanol.