Diethyl Ether → HCID 10130730, compound

Participants

Reaction Steps

In a dry 100 mL Schlenk-tube, which has been flooded with argon, adipic acid dipent-3-inyl ester (135 mg, 485 μmol), complex 23a.OEt2 (10.5 mg, 9.67 μmol, 2 mol %) and molecular sieve (970 mg, 5 Å, powder) were suspended in 24.2 mL of toluene. The reaction solution was stirred for 24 h at room temperature, was filtered for the processing over a short silica gel column, the filtrate was concentrated and the residue was purified by means of column chromatography (SiO2, hexane/EtOAc, 20:1). One obtains 1,8-dioxacyclotetradec-11-in-2,7-dione (100 mg, 92%) as colorless solid. M.p.=109-110° C.; 1H NMR (400 MHz, CD2Cl2): δ=4.13-4.06 (m, 4H), 2.53-2.47 (m, 4H), 2.39-2.30 (m, 4H), 1.76-1.67 (m, 4H); 13C NMR (100 MHz, CD2Cl2): δ=173.2 (2×C), 78.2 (2×C), 62.8 (2×CH2), 35.2 (2×CH2), 25.4 (2×CH2), 19.4 (2×CH2); IR (film): v=2995, 2954, 2937, 2918, 2901, 2872, 1721, 1458, 1425, 1384, 1341, 1272, 1236, 1167, 1140, 1080, 1065, 1021, 981, 931, 843, 124, 699 cm−1; MS (EI) m/z (%): 129 (3), 111 (8), 78 (100), 66 (20), 55 (15), 41 (8); HRMS (ESI): m/z: calculated for C12H16O4+Na: 247.0941; found: 247.0938.

Provenance & Evidence