Tetrabutylammonium Fluoride → HCID 17981372, compound

Participants

Reaction Steps

Tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 13.2 mL, 13.2 mmol) was added to a stirred solution of [4-(2-ethylhexyloxy)phenylethynyl]trimethylsilane (3) (2.59 g, 13.2 mmol) in tetrahydrofuran (70 mL) and the solution stirred under nitrogen at room temperature for 100 min. The solvent was removed and the residue passed through a plug of silica with dichloromethane—light petroleum (1:9) as eluent to give 1-(2-ethylhexyloxy)-4-ethynylbenzene (4) (1.96 g, 99%) as a pale yellow-brown oil. (Found: C, 83.4, H, 9.85, C19H30OSi requires C, 83.4; H, 9.6%); νmax(film)/cm−1 3294 and 3317 (C≡C—H) and 2107 (C≡C); δH(400 MHz, CDCl3) 0.94 (6 H, m, CH3), 1.28-1.57 (8 H, m, CHCH2CH2CH2CH3 and CHCH2CH3), 1.74 (1H, m, OCH2CH), 3.01 (1 H, s, CCH), 3.85 (2 H, d, J 5, OCH2CH), and 6.85 and 7.43 (4 H, AA′BB′, phenyl H); δc(100.6 MHz, CDCl3) 11.1, 14.1, 23.0, 23.8, 29.0, 30.4, 39.3, 70.5, 75.6, 83.8, 113.7, 114.4, 133.5, 159.8.

Provenance & Evidence