[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].S(O[CH2:22][CH:23]1[CH2:28][CH2:27][CH:26]=[CH:25][O:24]1)(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:22][CH:23]2[CH2:28][CH2:27][CH:26]=[CH:25][O:24]2)=[CH:4][CH:3]=1A mixture of a solution of 247 mg of p-fluorophenol in 1 ml of dimethylformamide with 87 mg of 55% sodium hydride was stirred at room temperature for 30 minutes. 537 mg of 2-tosyloxymethyl-3,4-dihydro-2H-pyran were then added to the mixture, which was allowed to react at 90° C. for 3 hours. Thereafter, the mixture was treated and the product purified essentially as described in Example 34(a) to give 102 mg of 2-(4-fluorophenoxymethyl)-3,4-dihydro-2H-pyran as a colourless oil.
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