[Mg].[F:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Cl.II.[C:13]1(=[O:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[Cl-].[NH4+]>C(OCC)C>[F:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][C:13]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1To a suspension of 16.05 g of magnesium turnings in 200 ml of anhydrous diethyl ether was added a solution of 71.34 ml of o-fluorobenzyl chloride in 250 ml of ether at a rate sufficient to maintain the pot temperature at about 30° C. while cooling the flask in an ice water bath. The reaction was initiated by addition of a few iodine crystals. After the completion of the addition the mixture was stirred under nitrogen at ambient temperature for 45 minutes, and thereafter a solution of 58.9 ml of cycloheptanone in 200 ml of ether was added over a 25 minute period, keeping the pot temperature at about 20° C. with cooling. After the addition the mixture was stirred at ambient temperature for 1 hour and thereafter cooled to 8° C. and treated with 500 ml of saturated ammonium chloride solution (cautiously at first). After 10 minutes of vigorous stirring, the mixture was poured into a separatory funnel, the phases were separated and the aqueous phase was extracted with ether (2×250 ml). The combined ether extracts were washed with 250 ml of saturated ammonium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuo to an oil weighing 109.94 g which crystallized to a solid (mp 35°-40° C.) after removal from high vacuum. A 10 g portion of this material was purified by preparative high performance liquid chromatography (HPLC hereafter) preparative using dichloromethane as a solvent; m.p. 35°-38° C.
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