[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH:8]1[O:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16](OC)=[O:17].O.[OH-].[Na+]>C(OCC)C.O1CCCC1>[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH:8]1[O:13][C:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][OH:17]Thereafter, 0.7 g of lithium aluminum hydride was suspended in 20 ml of diethyl ether, and a solution of 1.98 g of methyl β-dihydropyranyloxyisovalerate in 3 ml of diethyl ether was slowly dropwise added to the suspension, and a reaction was allowed to proceed at room temperature overnight. The mixture was further heated and refluxed for 1 hr and then cooled, and 0.7 ml of water, 0.7 ml of a 15% aqueous sodium hydroxide solution and 2.1 ml of water were successively added in that order with ice cooling. The mixture was stirred at room temperature for 1 hr, 20 ml of tetrahydrofuran was added thereto, and the mixture was stirred for additional one hr. The precipitat was collected by filtration and washed with 10 ml of tetrahydrofuran, and the washing was combined with the filtrate. The solvent was removed from the combined filtrate and washing by distillation under a reduced pressure to obtain 1.32 g of crude 3-dihydropyranyloxy-3-methyl butanol.
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