Phenol → Diethyl 2-{3-[3-(1-Octynyl)phenoxy]propyl}propan-1,3-dioate

Participants

Reaction Conditions

Reaction Steps

1-(3-Hydroxyphenyl)-oct-1-yne, (2.20 g, 0.01M) and diethyl 2-(3-hydroxypropyl)propane-1,3-dioate [2.40 g, 0.01M, (prepared by the method of A.G. Just et al, Tet. Letts., 3645-3647, (1979)] were dissolved in dry tetrahydrofuran, (50 ml) and triphenylphosphine, (4.20 g, 0.016M), added. The solution was stirred at 10° C. and diethyl azodicarboxylate, (2.80 g, 0.016M), added dropwise. The reaction was stirred for 0.5 h after which time TLC showed some unreacted phenol remaining. Further aliquots of the alcohol, (2.40 g, 0.01M), triphenylphosphine, (4.20 g, 0.016M) and dietyl azodicarboxylate (2.80 g, 0.016M) were added and the reaction stirred for 0.5 h. Evaporation of the solvent in vacuo gave a red oil which was purified by chromatography on silica gel eluting with dichloromethane→chloroform, to yield 0.770 g (19%) of the title compound as a colourless oil. νmax (film 1580, 1600, 1610, 1740, 1758, 2225 (weak) cm-1 ; δ(CDCl3) 0.87 (3H, distorted t, terminal CH3), 1.26 (6H, t, J 7 Hz, 2×ester CH3), 1.33 (8H, m, alkylene chain), 1.93 (4H, m, OCH2CH2CH2), 2.34 (2H, t, J 6 Hz, acetylenic CH2), 3.37 (1H, t, J 7 Hz, CH), 3.91 (2H, t, J 6 Hz, OCH2), 4.16 (4H, q, J 7 Hz, 2×ester CH2), 7.00 (4H, m, aromatics).

Provenance & Evidence