[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([OH:20])[CH2:19][CH2:18][C:13]3([O:17][CH2:16][CH2:15][O:14]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.I[CH3:22]>C1COCC1>[CH3:22][O:20][C:10]1([C:7]2[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=2)[CH2:11][CH2:12][C:13]2([O:14][CH2:15][CH2:16][O:17]2)[CH2:18][CH2:19]1Sodium hydride (1.27 g, 31.7 mmole) was added to a solution of 8-(4-fluoro-phenyl)-1,4-dioxaspiro[4.5]decan-8-ol (8.0 g, 10 mmole) in THF (100 ml) and the mixture stirred for 16 hr and heated at reflux for 4 hr. The solution was cooled to 25° C. and iodomethane (6.75 g, 47.6 mmole) was added. The mixture was stirred for 112 hr and concentrated in vacuo. The residue was suspended in water and the mixture extracted with methylene chloride. The extracts were dried and concentrated in vacuo to give 8-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol methyl ether (98.8%, mp: 52°-54° C.).
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