1-Tridecyne → Diethyl 2-[2-(1-tridecynyl)phenyl]methylpropan-1,3-dioate

Participants

Reaction Steps

Reaction of diethyl(2-bromobenzyl)propan-1,3-dioate (11.87 g, 30 mmol) with 1-tridecyne (11.10 g, 45 mmol) as described in example 3 gave 3.89 g (29%) of the title compound as a pale yellow oil after chromatography. It had νmax (film) 1735, 1755, 2840, 2920 cm-1 ; δ(CDCl3) 0.87 (3H, distorted t, terminal CH3), 1.08 (6H, t, J 7 Hz, ester CH3), 1.28 (18H, m, alkylene chain), 2.42 (2H, t, J 6 Hz, C≡C--CH2), 3.31 (2H, d, J 7.5 Hz, ArCH2), 3.90 (1H, t, J 7.5 Hz, methine H), 4.12 (4H, q, J 7.5 Hz, ester CH2), 7.15 (3H, m, aromatics), 7.36 (1H, m, aromatic). M+ 428.2928 (C27H40O4 requires; 428.2926).

Provenance & Evidence