Water → HCID 23557343, compound

Participants

Reaction Steps

To a solution of suberic acid monomethyl ester (1.00 g, 5.31 mmol) in THF (15 mL) was added oxalyl chloride (2 mL) followed by DMF (1 drop). The solution was stirred for 2 h, then concentrated under reduced pressure. Volatiles were removed under high vacuum overnight, leaving a yellow oil (1.08 g, 5.22 mmol, 98%). This crude acid chloride was then transformed into the trifluoromethyl ketone by a literature method as follows. (65) To a solution of the acid chloride (1.08 g, 5.22 mmol) in CH2Cl2 (45 mL) at 0° C. were added trifluoroacetic anhydride (4.64 mL, 32.81 mmol) and pyridine (3.54 mL, 43.74 mmol). The mixture was allowed to warm to ambient temperature and stirred for 2 h. After returning to 0° C., ice-cold H2O (20 mL) was added carefully. Additional H2O (100 mL) was added and the layers separated. The aqueous phase was extracted with CH2Cl2 (2×30 mL) and the organic layers combined, washed with brine, dried over MgSO4, and filtered. Evaporation under reduced pressure left a brown oil, which was purified by flash chromatography (2-4% MeOH/CH2Cl2) to give 71 as a clear oil (641 mg, 2.67 mmol, 49%). TLC Rf 0.24 (2% MeOH/CH2Cl2); 1H-NMR (400 MHz, CDCl3) δ 3.67 (s, 3H), 2.71 (t, 2H), 2.31 (t, 2H), 1.65 (m, 4H), 1.35 (m, 4H).

Provenance & Evidence