Ethyl Acetate → HCID 21876949, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-cyclopentyloxythien-2-ylmethyl)-nitrobenzene (1.28 g, 4.2 mmol) in absolute ethanol (34 mL) was added tin dichloride hydrate (4.76 g, 21.2 mmol) at 20-25° C. under nitrogen. The mixture was heated at 75° C. for 2.5 hours and cooled to 0-5° C. Saturated sodium bicarbonate was added to pH 8. Ethyl acetate was added and the mixture was filtered. The layers were separated, and the aqueous phase was extracted with additional ethyl acetate. The combined organic phases were washed with brine, dried (Na2SO4), and concentrated to dryness. Purification by flash chromatography (silica, hexane/ethylacetate) gave 4-(4-cyclopentyloxythien-2-ylmethyl)-phenylamine (0.47 g, 41%) as a pale yellow oil; 1H NMR (300 MHz, CDCl3) δ 7.03 (d,J=8.5Hz, 2H), 6.63 (d,J=8.5Hz 2H), 6.41 (m,1 H), 5.96 (d,J=1.7Hz,1 H, 4.58 (quintet, J=4.3 Hz, 1 H), 3.91 (S,2H), 3.59 (bs,2H), 1.67-1.88 (m, 6H), 1.46-1.67 (m, 2N).

Provenance & Evidence