Hydrochloric Acid → 1,1,1-Trifluoro-3-nitro-2-pentanol

Participants

Reaction Conditions

Reaction Steps

1-Nitropropane (3.25 g, 36.6 mmol), trifluoroacetaldehyde ethyl hemiacetal (5.85 g, 36.6 mmol, 90% purity) and powdered K2CO3 (0.34 g, 2.5 mmol) were mixed and stirred at 60° C. for 3 h and then at room temperature for 3 days. Brine (10 ml) and 1N aqueous HCl (10 ml) were added and the lower organic layer separated. The aqueous layer was extracted with ether (2×30 ml) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by flash chromatography on silica gel with a gradient elution of CH2Cl2:hexane (50:50), CH2Cl2:hexane (75:25), CH2Cl2 (100%) and MeOH:CH2Cl2 (5:95) to give the product as a waxy white solid (4.4 g, 64%). δH (CDCl3, 500 MHz) 1.04-1.00 (3 H, m, CHCH2CH3), 2.16-1.99 (2 H, m, CHCH2CH3), 4.37 (1 H, s, b, OH), 4.71-4.59 (2 H, m, 2×CH); δC (CDCl3, 500 MHz) dq (126.79, 126.70; 124.55, 124.46; 122.30, 122.21; 120.06, 119.96, CF3), two peaks (88.34, 87.60 CH NO2), eight peaks (71.13, 70.87, 70.81, 70.62, 70.56, 70.36, 70.30, 70.05 CHOH), two peaks (23.57 and 21.98 CH2), two peaks (9.77 and 9.66 CH3); 71.5 (CH), 54.03 (CH), 25.5 (CH2), 11.05 (CH3). 19F NMR δ −76.2 and −77.5

Provenance & Evidence