Ammonium Chloride → Ethyl 2-(7-chloro-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-hydroxyacetate

Participants

Reaction Steps

A solution of ethyl 2-(7-chloro-1-(4-chlorophenyl)-3-methyl-naphthalen-2-yl)-2-oxoacetate (26 mg, 67 μmol) in EtOH (absolute, 1.0 mL) and DCM (1.0 mL) was treated with NaBH4 (5.1 mg, 0.134 mmol) at 23° C. After 1 h, saturated NH4Cl (1.0 mL) was added. The reaction was stirred overnight, then diluted with H2O (10 mL). The mixture was extracted with DCM (3×), and the combined organics dried (Na2SO4), filtered, and concentrated, giving the title compound (28 mg, >99% yield). 1H-NMR: (400 MHz, CDCl3): δ 7.72 (d, J=8.6 Hz, 1H), 7.65 (s, 1H), 7.51-7.22 (m, 6H), 5.19 (s, 1H), 4.35-4.17 (m, 2H), 2.49 (s, 3H), 1.20 (t, J=7.0 Hz, 3H).

Provenance & Evidence