Potassium sodium tartarate → HCID 18782828, compound

Participants

Reaction Steps

3-(3-Ethyl-2,2-dimethyl-cyclobutyl)-but-3-en-2-one (568 mg, 3.46 mmol) was dissolved in benzene (20 ml) under an atmosphere of dry N2. To the solution was added a 1.0 M solution of diethylaluminum cyanide (5.0 ml) in toluene. After stirring at ambient temperature for 30 minutes, a 10% aqueous solution of potassium sodium tartrate (20 ml) was added to the reaction. After stirring at ambient temperature for 30 minutes, the reaction was partitioned between CH2Cl2 and 0.1 N aqueous sodium hydroxide (NaOH). The CH2Cl2 layer was washed with brine, dried over MgSO4, filtered and concentrated under vacuum to give 551 mg of the titled compound as an oil: 1H NMR (CDCl3)δ 3.99 (dt, J=4.3, 11.0 Hz, 1H), 3.14 (dd, J=3.1, 4.6 Hz, 1H), 2.62 (m, 1H), 2.53 (m, 1H), 2.41 (m, 1H), 2.22 (m, 1H), 2.17 (s, 3H), 2.01 (m, 1H), 1.44 (d, J=10.6 Hz, 1H), 1.22 (s, 3H), 0.64 (s, 3H).

Provenance & Evidence