Diethyl Ether → HCID 44251362, compound

Participants

Reaction Conditions

Reaction Steps

A 3-necked 500 mL RBF is charged with triethylsilylacetylene (6.1 mL, 34.11 mmol) and anhydrous diethyl ether (100 mL) under nitrogen. The solution is cooled to 0° C. and a solution of 2.5 M n-butyllithium in hexanes (12.4 mL, 31.01 mmol) is added dropwise. The reaction mixture is removed from the ice-bath and stirred for 1 h at 22° C. 1,4,8,11-Tetramethyl-6,13-pentacenequinone 8 (1.13 g, 3.10 mmol) is added and the reaction mixture is stirred at 22° C. for 2 h. Anhydrous tetrahydrofuran (100 mL) is added and the reaction mixture is stirred for a further 18 h. A saturated solution of stannous(II) chloride in 10% HCl solution (20 mL) is added and the solution is stirred under nitrogen for 30 mins. The reaction mixture is poured into water (300 mL) and extracted with dichloromethane (300 mL). The aqueous layer is re-extracted with dichloromethane (2×100 mL). The combined extracts are dried over sodium sulfate and concentrated in vacuo. The crude product is dissolved in a small volume of dichloromethane, acetone (100 mL) is added, and the mixture is stirred for 30 mins. The solid is filtered off, washed with cold acetone and methanol, and dried under vacuum to yield the product 9 as a dark blue solid (1.15 g, 61%): 1H-NMR (300 MHz, CDCl3) δ9.40 (s, 4H), 7.16 (s, 4H), 2.82 (s, 12H), 1.30 (t, 18H, 3J=8 Hz), 0.94 (q, 12H, 3J=8 Hz); 13C-NMR (75 MHz, CDCl3) δ 132.8, 132.4, 130.1, 125.9, 123.2, 118.2, 107.6, 104.1, 19.6, 8.0, 4.8.

Provenance & Evidence