HCID 10988699, compound → 1,6-dioxacyclododec-9-yne-2,5-dione

Participants

Reaction Conditions

Reaction Steps

In a dry 100 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3)(bipy)] (109.2 mg, 0.10 mmol) and MnCl2 (12.6 mg, 0.10 mmol) were suspended in dry toluene (15 mL) and the mixture was heated to 80° C. Additional dry toluene (35 mL) and succinic acid dipent-3-inyl ester (278.3 mg, 1.00 mmol) were added after 30 min, the reaction mixture was stirred for 24 h at 80° C. and was filtered after cooling over a short silica gel column. The filtrate was concentrated and the residue was purified by column chromatography (hexane/EtOAc 4:1). 1,6-dioxacyclododec-9-ine-2,5-dione was isolated as colorless oil (yield: 81%). 1H NMR (400 MHz, CD2Cl2): δ=4.21-4.14 (m, 4H), 2.61 (s, 4H), 2.44-2.37 (m, 4H); 13C NMR (100 MHz, CD2Cl2): δ=171.9 (2×C), 79.0 (2×C), 61.6 (2×CH2), 30.2 (2×CH2), 19.7 (2×CH2); IR (film): v=2965, 2915, 2840, 1729, 1458, 1421, 1383, 1353, 1336, 1267, 1251, 1158, 1053, 1030, 1000, 952, 837 cm−1; MS (EI) m/z (%): 166 (1), 101 (14), 78 (100), 66 (59), 65 (16), 55 (7), 40 (12), 28 (7); HRMS (ESI): m/z: calculated for C10H12O4+Na: 219.0628; found: 219.0627.

Provenance & Evidence