Diisopropylamine → HCID 59695627, compound

Participants

Reaction Steps

To a solution of diisopropylamine (21.6 ml, 154.0 mmol) in 200 ml of anhydrous diethyl ether was added 2.5 M n-BuLi in hexane (49.3 ml, 123.3 mmol) at room temperature. After stirring at room temperature for 30 min, the resulting lithium di-isopropylamide (LDA) solution was cooled to −76° C. A solution of 3-butylthiophene (18.0 g, 123.3 mmol) in 100 ml of ether was cooled to −76° C. and added to the above LDA solution. The temperature was allowed to rise slowly to −40° C., whereupon it was stirred for 1 h. The solution was then recooled to −76° C. and trimethylborate (20.6 ml, 185.0 mmol) was added slowly. The mixture was allowed to warm to room temperature and stirred for 2 h. After quenching with 10% HCl (180 ml) the organic layer was separated and the aqueous layer was extracted with ether (2×). The combined organic layer was dried over MgSO4, filtered and concentrated. The residue was added to 1,3-propanediol (8.9 ml, 123.3 mmol) and refluxed for 2 h. The mixture was then placed directly on a silica column and eluted first with hexane, then chloroform to give the product, 8.46 g, 31%. 1H NMR (CDCl3-d3, 500 MHz): δ 7.36 ppm (s, 1 H), 7.12 ppm (s, 1 H), 4.14-4.12 ppm (t, 4 H, J=8.6 Hz), 2.60-2.63 ppm (t, 2 H, J=8.6 Hz), 2.04 ppm (m, 2 H), 1.35 ppm (m, 2 H), 1.32 ppm (m, 2 H), 0.89 ppm (t, 3 H, J=7.5 Hz); 13C-NMR (CDCl3, 500 MHz): δ 144.4, 136.8, 126.5 126.4, 62.1, 32.85, 29.73, 27.46, 22.45, 13.90 ppm. EI, MS m/z (%): 224 (100, M+).

Provenance & Evidence