Phenylacetaldehyde → HCID 68828540, compound

Participants

Reaction Steps

Phenacetaldehyde 87 mg (0.72 mmol) and 190 mg (0.72 mmol) of 10 were mixed in 1,2-dichloroethane (15 mL) and then treated with sodium triacetoxyborohydride 230 mg (1.08 mmol). The reaction mixture remained cloudy throughout the reaction. The mixture was stirred at room temperature under N2 atmosphere for 2 h. The reaction mixture was quenched by adding saturated NaHCO3, and the product was extracted with EtOAc. The EtOAc extract was dried (MgSO4), and the solvent was evaporated to give 0.25 g (95%) of a light yellow oil. Purification by chromatography on alumina using 10% ethyl acetate/hexane gave 0.23 g (89%) of desired product 11 as colorless clear viscous oil: 13C NMR (300 MHz, CDCl3) δ 158.9, 129.1, 128.6, 128.1, 126.2, 122.5, 117.1, 109.9, 63.2, 61.1, 55.5, 43.1, 37.4, 36.3, 34.0, 30.7, 22.4, 22.1.

Provenance & Evidence