Sodium Hydroxide → HCID 66670136, compound

Participants

Reaction Steps

To a solution containing 65 (2.2 g, 0.006 mol) in MeOH (15 mL) was added 1M NaOH (6 mL, 0.006 mol) at 0° C. After 30 min, TLC analysis revealed complete consumption of 65 [EtOAc/hexanes 1:1, Rf(65) 0.6; Rf(66)=0.5]. The solvent was removed in vacuo and the residue was dissolved in EtOAc. The organic phase was washed with 1M HCl, water, brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 2.11 g (quant.) of crude 66 which was used in the next step without further purification. 1H NMR (CDCl3, 300 MHz) δ9.0 (s, 1H, major rotamer), 8.85 (s, minor rotamer), 7.62-7.5 (m, 1H), 7.1-6.72 (m, 3H), 3.8-2.7 (m, 5H), 2.15-1.3 (m, 3H), 1.55 (s, 9H), 0.85 (d, J=7 Hz, 3H) ppm.

Provenance & Evidence