C[O-].[Na+].[N:4](OCCC(C)C)=[O:5].[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:24])[CH2:21][CH2:22][CH3:23])=[CH:16][CH:15]=1>CO.O1CCCC1>[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:24])[C:21](=[N:4][OH:5])[CH2:22][CH3:23])=[CH:16][CH:15]=111.0 g (0.206 mol) of sodium methoxide is suspended in 130 ml of methanol. Then isoamyl nitrite (27 ml, 0.206 mol) and 25 g (0.129 mol) of 1-(4-Methylsulfanyl-phenyl)-butan-1-one dissolved in 70 ml of tetrahydrofuran (THF) are added and the reaction solution is stirred at room temperature for 1.5 days. After concentrating, water and acetic acid are added to neutralise. The crude product is extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (15:85) as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ[ppm]: 1.14 (t, 3H), 2.52 (s, 3H), 2.72 (q, 2H), 7.25 (d, 2H), 7.89 (d, 2H), 8.01 (s, 1H).
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