Dimethylformamide → HCID 21882247, compound

Participants

Reaction Conditions

Reaction Steps

The dinitrile 3 (1.39 g; 6.58 mmol) in DMF (25 mL) was treated with butyl bromide (2.0 mL; 2.55 g; 19 mmol) followed by freshly dried potassium carbonate (2 g) and then the resulting mixture was stirred at 50° C. overnight. After this time ethyl acetate (200 mL) was added and the whole was poured onto water (200 mL) and shaken. After separating the layers, the aqueous layer was extracted with more ethyl acetate (100 mL) and then the combined organic layers were washed with water (3×250 mL), dried (MgSO4), and evaporated to dryness. The remaining solid was triturated with boiling hexane and filtered to give the dibutyl ether 4 as a pale-brown powder (944 mg; 44%). 1H NMR (CDCl3) δ 1.01 [3H, t, J=7.4 Hz, CH3 (Bu)]; 1.03 [3H, t, J=7.4 Hz, CH3 (Bu)]: 1.53–1.66 [4H, m, CH2 (Bu)]; 1.87–1.96 [4H, m, CH2 (Bu)]; 4.52 (2H, t, J=6.5 Hz, OCH2Pr); 4.66 (2H, t, J=6.7 Hz, OCH2Pr); 7.65 (1H, dd, J=8.5, 4.2 Hz, Ar—H); 8.57 (1H, dd, J=8.5, 1.6 Hz, Ar—H); 9.10 (1H, dd, J=4.2, 1.6 Hz, Ar—H)

Provenance & Evidence