[H-].[Al+3].[Li+].[H-].[H-].[H-].COC(CCC([O:15][C:16]1[C:17]([CH3:33])=[C:18]([CH3:32])[C:19]2[O:23][CH:22]([CH2:24][CH2:25][C:26](OC)=[O:27])[S:21][C:20]=2[C:30]=1[CH3:31])=O)=O.C(OCC)(=O)C.Cl>O1CCCC1>[OH:15][C:16]1[C:17]([CH3:33])=[C:18]([CH3:32])[C:19]2[O:23][CH:22]([CH2:24][CH2:25][CH2:26][OH:27])[S:21][C:20]=2[C:30]=1[CH3:31]10 g of lithium aluminum hydride were suspended in 500 ml of dried tetrahydrofuran, and then a solution of 32.0 g of methyl 3-[5-(3-methoxycarbonylpropionyloxy)-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propionate (prepared as described in Example 31) in 160 ml of tetrahydrofuran was added dropwise with stirring and ice-cooling and under a nitrogen stream to the suspension. After the dropwise addition, the reaction mixture was stirred for 1 hour at room temperature and then refluxed for 4 hours. The reaction mixture was then cooled with ice-water, after which a mixture of 10 g of ethyl acetate and 50 ml of tetrahydrofuran was added dropwise, and the mixture was stirred for 1 hour at room temperature, after which aqueous tetrahydrofuran was added dropwise. The reaction mixture was then poured into ice-water. The pH of the mixture was adjusted to an acid value by the addition of a 10% w/v aqueous solution of hydrochloric acid, and the precipitating product was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting crude product was subjected to silica gel column chromatography and the title compound, melting at 116.5°-117° C., was obtained from the fraction eluted with a 9:1 by volume mixture of benzene and ethyl acetate.
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