Sodium Hydroxide → HCID 22040478, compound

Participants

Reaction Conditions

Reaction Steps

A flame dried 500 mL three necked round bottom flask purged with N2 was charged with LAH (3.0 g, 75.0 mmol) and dry THF (240 mL). The resulting suspension was cooled to 0° C. and t-butyl ester 1 (20.7 g, 60 mmol) was slowly added while keeping the internal reaction temperature under 5° C. Reaction stirred at 0° C. for 2 hr followed by stirring at RT for overnight. NaBH4 (2.27 g, 60 mmol) was added and stirred for an additional hour at rt. After the reaction was judged complete, the stirred reduction mixture was treated with successive dropwise addition of 3 mL H2O, 3 mL NaOH, and 9 mL H2O. Reaction mixture filtered through Celite, washed with ethyl acetate and methanol, and evaporated. Crude product absorbed onto silica gel and chromatographed using 97:3 CH2Cl2/MeOH to give 2 as an orange solid. 1H NMR (300 MHz, CDCl3) δ 8.40 (d, J=5.5 Hz, 1H), 8.05 (br s, 1H), 7.96 (d, J=2.75 Hz, 1H), 7.29 (d, J=2.75 Hz, 1H), 6.92 (d, J=9.35 Hz, 1H), 6.75 (m, 2H), 4.68 (s, 2H), 3.07 (d, J=5.23 Hz, 3H).

Provenance & Evidence