Ethyl 5-(3-acetyloxyphenylthio)-4-oxopentanoate → Ethyl 3-(6-hydroxybenzo[B]thiophen-3-YL)propanoate

Participants

Reaction Conditions

Reaction Steps

Concentrated sulfuric acid (20 ml) was cooled in an ice-water bath to 0° C. and added to a flask containing ethyl 5-(3-acetyloxyphenylthio)-4-oxopentanoate (920 mg, 3.4 mmol) at 0° C. The reaction was stirred at 0° C. for 15 minutes, and then poured over ice. The mixture was extracted with ethyl acetate, dried, filtered, and evaporated under vacuum to yield 700 mg (82%) of Ethyl 3-(6-hydroxybenzo[b]thiophen-3-yl)propanoate. NMR 1H DMSO-d6 δ: 9.59 (s, 1H), 7.59 (d, 1H, J=8.4 Hz), 7.25 (d, 1H, J=2.4 Hz), 7.08 (s, 1H), 6.89 (dd, 1H, J=2.4, 8.4 Hz), 4.06 (c, 2H, J=7.2 Hz), 2.99 (t, 2H, J=6.8 Hz), 2.70 (t, 2H, J=6.8 Hz), 1.16 (t, 1H, J=7.2 Hz).

Provenance & Evidence