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

Participants

Reaction Steps

To a stirred solution of 35 (6.30 g, 12.9 mmol) in 1:1 THF/TEA (26 mL) in a Parr apparatus was added a catalytic amount of 20% Pd/C (0.05 g). The reaction vessel was purged with hydrogen then pressurized to 70 psi. After stirring for 16 h the reaction mixture was filtered through a 4 cm pad of celite and concentrated under reduced pressure to afford 36 as a brown oil (5.80 g, 98%): 1H NMR (300 MHz, CDCl3) δ 6.75 (d, J=8.9 Hz, 2H), 6.62 (d, J=8.9 Hz, 2H), 4.71-4.55 (m, 1H), 4.09-4.00 (m, 2H), 3.94-3.31 (m, 22H), 1.93-1.44 (m, 6H).

Provenance & Evidence