[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH3:14])=[C:7]([SH:13])[C:8]=2[CH3:12])[O:3]1.[OH-].[Na+].[N+:18]([CH3:21])([O-:20])=[O:19].Cl>O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+].CCOCC>[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH3:14])=[C:7]([S:13][CH2:21][N+:18]([O-:20])=[O:19])[C:8]=2[CH3:12])[O:3]1The thiol (B) was added to a solution of sodium hydroxide (2.8 g, 70 mM) in water (30 ml) and stirred vigorously for 30 minutes. Nitromethane (2.3 ml, 42.5 mM) was added, followed immediately by ether (75 ml). The reaction mixture was cooled to 15° C. in a cold water bath, then a solution of potassium ferricyanide (17.2 g, 52.3 mM) in water (43 ml) was added in a steady stream and the reaction mixture was stirred at ambient temperature overnight. The mixture was acidified with 2M hydrochloric acid and extracted with ethyl acetate. The extracts were washed with water, brine, then dried (Na2SO4) and evaporated. The residual oil was purified by flash chromatography, eluting with hexane/toluene (4:1 v/v, increasing in polarity to 2:1 v/v), to give 2,2,5,7-tetramethyl-6-(nitromethylthio)chroman (3.1 g, 32% yield) as a gum; NMR: 1.3(6H,s), 1.82(2H,t), 2.4(6H, 2d), 2.61(2H,t), 5.18(2H,s), 6.6(1H,s).
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