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

HRID 985480Notes

Reaction equation

C([O:4][C:5]1[CH:6]=[C:7]([S:11][CH2:12][C:13](=O)[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]=[CH:9][CH:10]=1)(=O)C>S(=O)(=O)(O)O>[OH:4][C:5]1[CH:10]=[CH:9][C:8]2[C:13]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][S:11][C:7]=2[CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

additionadded to a flask
additionpoured over ice
extractionThe mixture was extracted with ethyl acetate
customdried
filtrationfiltered
customevaporated under vacuum

Sources & evidence

ORD record: ord-cb778d4c3ce04aa8ad2e133460e72555
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872730B2

Reaction notes

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