[CH2:1]([O:4][CH2:5][CH2:6]Cl)[CH2:2]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[O:16]=[C:17]([CH3:23])[CH2:18][C:19]([O:21][CH3:22])=[O:20]>O.CN(C)C=O>[C:17]([C:18]1([C:19]([O:21][CH3:22])=[O:20])[CH2:6][CH2:5][O:4][CH2:1][CH2:2]1)(=[O:16])[CH3:23]
In a flask made of glass having an inner volume of 1000 ml and equipped with a stirring device, a thermometer, a dropping funnel and a reflux condenser were charged 143 g (1.0 mol) of 2,2′-dichloroethyl ether, 276 g (2.0 mol) of anhydrous potassium carbonate, 10 g (0.06 mol) of potassium iodide and 600 ml of N,N-dimethylformamide, and the temperature of the mixture was raised to up to 80° C. with stirring. Then, 139 g (1.2 mol) of methyl 3-oxobutanoate was gently added dropwise to the mixture, and the mixture was reacted at the same temperature for 8 hours. After completion of the reaction, 1000 ml of water was added to the reaction mixture, and the resulting mixture was extracted three times with 600 ml of ethyl acetate. The organic layers were dried over magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure (125 to 127° C., 1.3 kPa) to give 95 g (Isolation yield: 50%) of 4-acetyl-4-methoxycarbonyltetrahydropyran with a purity of 98% (areal percentage by gas chromatography) as a pale yellow liquid.
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