Hydrochloric Acid → 2,2,5,7-Tetramethyl-6-(nitromethylthio)chroman

Temperature

15 °C

The 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).

1. stirringthe reaction mixture was stirred at ambient temperature overnight
2. extractionextracted with ethyl acetate
3. washThe extracts were washed with water, brine
4. dry with materialdried (Na2SO4)
5. customevaporated
6. customThe residual oil was purified by flash chromatography
7. washeluting with hexane/toluene (4:1 v/v, increasing in polarity to 2:1 v/v)

ORD record

ord-4d2b45baa8024de28c2b55d98f55883b

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05185452