4-Nitrophenol → 2-(17-(4-Nitrophenoxy)-3,6,9,12,15-pentaoxaheptadecyloxy)tetrahydro-2H-pyran

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 34 (7.03 g, 13.5 mmol) in anhydrous DMF (24 mL) were added K2CO3 (5.60 g, 40.5 mmol), and 4-nitrophenol (1.88 g, 13.5 mmol). The reaction mixture was heated to 80° C. for 16 h. Upon completion, the reaction mixture was diluted in water, extracted three times with CH2Cl2, and then dried over MgSO4. The filtrate was concentrated under reduced pressure to give an oily residue, which provided 35 as a yellow oil without further purification (6.30 g, 96%): 1H NMR (300 MHz, CDCl3) δ 8.19 (d, J=9.3 Hz, 2H), 6.97 (d, J=9.3 Hz, 2H), 4.67-4.57 (m, 1H), 4.26-4.17 (m, 2H), 3.95-3.79 (m, 2H), 3.78-3.34 (m, 22H), 1.47-1.84 (m, 6H).

Provenance & Evidence