Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])([CH3:12])[CH2:7][CH2:8][S:9]2)=[CH:4][CH:3]=1.C([Li])CCC.CON(C)[C:22](=[O:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C1COCC1>[CH3:12][C:6]1([CH3:13])[C:5]2[C:10](=[CH:11][C:2]([C:22](=[O:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:3][CH:4]=2)[S:9][CH2:8][CH2:7]1A solution of 7-bromo-4,4-dimethyl-thiochroman (2.0 g, 7.78 mmole) in 45 mL of THF at −78° C. was, treated with 3.9 mL of 2.5M butyllithium. After 30 minutes at −78° C. a solution of hexanoic acid methoxy-methyl-amide (1.486 g, 9.33 mmole) in 5 mL of THF was added. The reaction mixture was stirred at −78° C. for 30 minutes, warmed to room temperature, quenched by the addition of 50 mL of saturated aqueous ammonium chloride solution and extracted with three 50 mL portions of ether. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 3% ethyl acetate in hexanes) to yield 1.183 g of 1-(4,4-dimethyl-thiochroman-7-yl)-hexan-1-one as a pale yellow oil.
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