Cyclopropanecarboxaldehyde → HCID 66868045, compound

Participants

Reaction Steps

To a stirred solution of 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (0.69, 3.0 mmol) in anhydrous THF (10 ml) at −78 C under an N2 atmosphere was added dropwise a solution of lithium diisopropylamide (1.75 ml of a 1.8M solution in THF/heptanes/ethyl benzene, 3.15 mmol). The reaction was stirred at −78 C for 60 minutes and then cyclopropanecarbaldehyde (0.27 ml, 3.6 mmol) was added dropwise. The reaction was stirred at −78 C for a further 30 minutes and then allowed to warm to room temperature over 210 minutes. The reaction was quenched by addition of H2O (50 ml) and extracted with EtOAc (50 ml). The organic phase was washed with H2O (50 ml) and brine (50 ml), dried over MgSO4, filtered and evaporated to dryness under reduced pressure to give a brown oil (1.37 g). The crude material was purified by flash chromatography over SiO2 using a 100% isohexane to 100% EtOAc gradient to give the desired product (mix of diastereomers) as a colourless oil (622 mg).

Provenance & Evidence