HCID 10997724, compound → HCID 59875688, compound

Participants

Reaction Steps

Ethyl (E)-2,2-dimethyl-3-ethyl-3-pentenoate 23 (35.58 g, 193 mmol) is added dropwise to a suspension of lithium aluminium hydride (12.1 g, 320 mmol) in 81 ml of THF. The mixture is refluxed for 3 h, stirred for 16 h at r.t. and quenched with ice. The precipitate is filtered off by suction, washed several times with diethyl ether and hydrolyzed with 1 M hydrochloric acid. The aqueous solution is extracted with diethyl ether (3×100 ml). The combined etheral extracts are dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by vacuum distillation affords the title compound 24 (15.87 g, 58%) as a colourless liquid (b.p. 105-106° C./30 mbar). 13C-NMR (100 MHz, CDCl3): δ=145.2; 120.5; 69.7; 42.0; 24.0; 20.0; 14.2; 13.6

Provenance & Evidence