Methyl morpholine oxide → HCID 21884137, compound

Participants

Reaction Steps

To a solution of 4-methoxy-1-(N-(2-propenyl)pentafluorophenylsulfonamido)benzene (101 mg, 0.26 mmol) in acetone:water (8:1, 1 mL) at rt was added N-methylmorpholine N-oxide (34.0 mg, 0.29 mmol) and OsO4 (0.10 mL of 0.16 M solution in H2O, 1.60×10−2 mmol). After stirring at rt for 18 h, the reaction mixture was treated with saturated NaHSO3 (5 mL) and allowed to stir at rt. After 1 h, the reaction mixture was poured onto saturated NaHSO3 (5 mL) and extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (MgSO4) and concentrated. Flash chromatography (1:1, 1:2/hexanes:EtOAc) afforded 90 mg (83%) of product as a white solid, mp 130–131° C. 1H NMR (CDCl3): d 7.11 (m, 2H), 6.85 (m, 2H), 3.78 (s, 3H), 3.90–3.65 (m, 5H). Anal. Calcd. for C16H13F5NO5S: C, 45.08; H, 3.07; N, 3.29; S, 7.52. Found: C, 45.09; H, 3.33; N, 3.27; S, 7.46.

Provenance & Evidence