Sodium Hydroxide → HCID 69414920, compound

Participants

Reaction Steps

Acetone (14 mL) in water (17 mL) was added with simultaneous addition of a separate solution of Oxone (5.96 g, 9.7 mmol) dissolved in EDTA solution (0.0004 M, 35 mL) to a solution of 72 (500 mg, 1.9 mmol), NaOH (170 mg, 4.2 mmol) and NaHCO3 (1.63 g, 19 mmol) in water (30 mL) at 0-2° C. The Oxone solution was added at twice the rate of the acetone solution, and care was taken to ensure that the internal temperature was kept below 8°. After stirring overnight, Na2S2O5 solution was added (10% w/v, 50 mL) and the mixture extracted with EtOAc. The extract was washed with brine, dried over MgSO4 and the solvent removed in vacuo. Chromatography of the crude material (silica gel, 2:3 EtOAc:petroleum) afforded 73 (149 mg, 31%): 1H NMR (CDCl3) δ 1.36 (mn, 4H), 1.63 (m, 4H), 2.33 (t, J=7 Hz, 2H), 2.69 (t, J=8 Hz, 2H), 7.44 (m, 2H), 8.02 (m, 2H). 13C NMR (CDCl3) δ 180.2, 148.5, 144.7, 134.9, 129.3, 123.3, 121.1, 35.6, 34.1, 31.0, 28.93, 28.88, 24.7.

Provenance & Evidence