Diethyl Carbonate → HCID 53963170, compound

Reaction equation

[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[CH3:11][CH:12]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[C:13](=[O:15])[CH3:14]>CCOCC>[CH3:11][CH:12]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[C:13](=[O:15])[CH2:14][C:3]([O:7][CH2:8][CH3:9])=[O:10]

Participants

Procedure

Into ether (800 ml), 52% paraffin solution of sodium hydride (22.8 g) is suspended, and diethyl carbonate (89.4 g) is portionwise added thereto while cooling with ice in nitrogen stream. Then, 3,7,11-trimethyl-6,10-dodecadien-2-one (88 g) is dropwise added thereto. After refluxing for 15 hours, the reaction mixture is poured into ice water. The ether layer is separated, washed with water, dried and evaporated. The residue is distilled under reduced pressure to give ethyl 3,7,11-trimethyl-6,10-dodecadien-2-one-1-carboxylate (81 g). B.P. 130° to 135°C/0.05 mmHg. IR: 1640, 1675, 1710, 1740 cm-1. NMR (carbon tetrachloride): 1.10 (d), 1.29 (t), 1.60 (s), 1.68 (s), 1.98 (s), 2.00-2.80 (broad), 3.33 (s), 4.15 (q), 4.8-5.3 (broad).