Citric Acid → 4-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzyl Alcohol

Participants

Reaction Steps

I2 (1.14 g, 4.5 mmol) was added to a MeOH (4 mL) solution of Et3N (1.2 mL) and 3-(4-((tert.-butyldimethylsilyloxy)methyl)phenyl)-3-(trifluoromethyl)-diaziridine (1.65 g, 5.00 mmol). The solution was stirred at rt (3 h). Aqueous citric acid 10% (50 mL) and NaS2O3 were added. The organic layer was extracted 3 times with ether (3×30 mL). The organic layers were combined, dried and concentrated in vacuum to obtain a yellow oil; 1H NMR (CDCl3): δ 0.09 (s, (CH3)2Si), 0.94 (s, CH3)3C), 4.74 (s, CH2), 7.15 (d, J=8.0 Hz, 2 C6H4), 7.35 (d, J=8.0 Hz, 2 C6H4). HCl in dioxane (4 M, 5 mL, 20 mmol) was added to a MeOH (10 mL) solution of the yellow residue. The solution was stirred at rt (3 h) and the volatiles were evaporated. The residue was purified by silica gel flash chromatography to obtain 840 mg (78%) of a yellow liquid: Rf=0.19 (1/9 EtOAc/hexanes); 1H NMR (CDCl3): δ 1.95-2.05 (br, OH), 4.70 (s, CH2), 7.18 (d, J=8.4 Hz, 2 C6H4), 7.38 (d, J=8.4 Hz, 2 C6H4); 13C NMR (CDCl3): δ 28.3 (q, J=40.4 Hz, C diazirine), 64.4 (CH2O), 122.1 (q, J=273.0 Hz, CF3), 126.7 (C6H2), 127.1 (C6H2), 128.3 (C6H2), 142.5 (C6H2).

Provenance & Evidence