Water → HCID 70652917, compound

Participants

Reaction Steps

To a solution of 12 (1.60 g, 5.0 mmol) in t-butanol (40 mL) and H2O (40 mL) AD-mix beta (8.6 g) was added portion wise at 5° C. The reaction was slowly warmed to room temperature and further stirred at this temperature for 16 hrs. The reaction mixture was cooled down to 5° C. and then quenched by adding excess sodium sulfite and stirred for 20 min. The resulting mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL×2). The organic layers were combined, washed with brine, dried over Na2SO4, and concentrated. The obtained residue was chromatographed on silica gel eluted with hexane/ethyl acetate (20%-100%) to afford 1.40 g (79%) of 13 as a colorless oil. 1H NMR (CD3OD) 1.50 (9 H, s), 2.60 (1 H, dd, J=7.77, 14.00), 2.82 (1 H, dd, J=4.60, 14.48 Hz), 3.35 (4 H, m), 3.49 (2 H, m), 3.56 (4 H, m), 3.76 (1 H, m), 7.38 (1 H, dd, J=1.96, 13.80 Hz), 7.90 (1 H, m). LC/MS (M+1) 356.

Provenance & Evidence