Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.[Li]CCCC.[CH3:15][C:16]1([CH3:28])[C:20](=[O:21])[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH2:17]1>C1COCC1>[CH3:15][C:16]1([CH3:28])[C:20]([C:2]2[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=2)([OH:21])[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH2:17]1To a −78° C. solution of p-bromothioanisole (5 g) in 100 mL of THF was added a solution n-BuLi (10 mL, 2.5 M in hexane). After stirring for 45 min. at −78° C., a solution of the product of Step 3 (2.4 g) in 10 mL of THF was added dropwise. The reaction mixture was stirred for 10 min. and then quenched with 100 mL of saturated solution of NH4Cl. The product was extracted with 300 mL of 2:1 hexanes/EtOAc. The extract was dried over Na2SO4 and concentrated. Th e residue was purified by chromatography eluting with 10:1 hexane/EtOAc to give 3.5 g of the title compound.
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