S(Cl)(Cl)=O.O[C:6]1([C:18]([F:21])([F:20])[F:19])[C:15]2[C:10](=[C:11]([CH3:16])[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][C:7]1=[O:17].C(OCC)(=O)C>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.CCCCCC>[CH3:16][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[CH:9]=[CH:8][C:7]([OH:17])=[C:6]2[C:18]([F:19])([F:20])[F:21]
Thionyl chloride (0.33 mL, 4.52 mmol) was added dropwise at about 5° C. to a stirred solution of 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone (1.04 g, 4.26 mmol) and 4-(dimethylamino)pyridine (3.5 mg) in pyridine (0.73 mL) under dry nitrogen. The reaction mixture was stirred and allowed to warm slowly to 25° C. (about 45 min). The reaction was judged to be complete by tlc using silica gel thin layer plates and 20% (v/v) ethyl acetate in hexane as the mobile phase. The reaction mixture was poured onto ice and extracted with diethyl ether. The ether extract was washed with water and a saturated solution of NaHCO3 in water, dried (MgSO4) and concentrated under reduced pressure to give the title compound (961 mg, 100% yield). A small sample, purified by sublimation (30°-34° C., 0.05 mm), had mp 83°-84° C.; nmr (CDCl3) δ 2.65 (s, 3H), 7.1 (d, J=9 Hz, 1H), 7.25 (m, 1H), 7.35 (q, J=8 Hz, 1H), 7.85 (m, 1H), 8.05 (d, J=9 Hz, 1H); uvλmax (MeOH) 335 nm (ε2,770), 322 (2,420), 293 (4,050), 281 (4,680), 222 (46,400); Anal Calcd for C12H9F3O: C, 63.72% H, 4.01%; Found: C, 63.47% H, 3.96%.
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