HCID 59316905, compound → HCID 59316961, compound

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of PCC (42.3 g, 196 mmol) and Celite (43 g) in DCM (300 mL) was cooled to 0° C. Alcohol 21.18 (35.0 g, 131 mmol) was slowly added to the reaction mixture over a period of 15 min. The reaction mixture was allowed to stir at room temperature for 2 h. The reaction mixture was then filtered through a pad of Celite and the filter bed was washed with DCM. Concentration of the filtrate gave a black tarry mass which was purified by flash chromatography (30-50% ethyl acetate-hexanes gradient) to give tert-butyl 3-(3-hydroxyphenyl)-3-oxopropylcarbamate 21.19 as pale yellow solid. Yield (20.3 g, 58%); 1H NMR (400 MHz, CDCl3) δ 9.78 (s, 1H), 7.27-7.40 (m, 2H), 7.01 (dd, J=8.0, 1.6 Hz, 1H), 6.80-6.83 (m, 1H), 3.22-3.27 (m, 2H), 3.08 (t, J=6.8 Hz, 2H), 1.36 (s, 9H).

Provenance & Evidence