Nitroethane → HCID 11356253, compound

Participants

Reaction Conditions

Reaction Steps

Following the procedure of One et al, J. Heterocyclic Chem., 1994, 31, 707-710, which is incorporated by reference, nitroethane (10 mL, 139.2 mmol, 96%) and 3-phenylpropionaldehyde (18.49 mL, 139.9 mmol) were dissolved in THF (70 mL, 2 M). After cooling to −10° C. in a brine bath, 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) (1.46 mL, 9.74 mmol) was added, and allowed to stir until complete by HPLC (75 min). The reaction was diluted with diethyl ether and H2O, and then the organic was removed and washed with saturated aqueous NaHCO3 and brine. The aqueous layers were back-extracted with diethyl ether, and the combined organics were dried with Na2SO4, filtered, and concentrated to provide 179, which was used without further purification in the next step. HPLC: 9.68 min. (Note: The retention time for the starting materials follow: nitroethane: 6.49 min.; 3-phenylpropionaldehyde: 9.45 min).

Provenance & Evidence