Acetic Acid → (2,3-Dihydro-benzo[b]thiophen-5-yl)-acetic acid

HRID 546257Notes

Reaction equation

[S:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[C:7](CC(N3CCOCC3)=S)[CH:8]=[CH:9][C:2]1=2.[C:19]([OH:22])(=[O:21])[CH3:20].S(=O)(=O)(O)O>O>[S:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[C:7]([CH2:20][C:19]([OH:22])=[O:21])[CH:8]=[CH:9][C:2]1=2

Participants

Conditions

Temperature: 100 °C

Procedure

In a round bottom flask with a reflux condenser was placed 2-(2,3-dihydro-benzo[b]thiophen-5-yl)-1-morpholin-4-yl-ethanethione (1.85 g, 6.62 mmol) and to it was added acetic acid (7.7 mL), concentrated sulfuric acid (1.1 mL) and water (2 mL). The reaction mixture was then heated at 100° C. for 4 h. After this time the solution was added to water (40 mL) and extracted with ethyl acetate (3×50 mL). The organics were dried over sodium sulfate, filtered and concentrated in vacuo. Purified using reverse phase HPLC to afford (2,3-dihydro-benzo[b]thiophen-5-yl)-acetic acid (525 mg, 41%) as a white solid.

Workup

customIn a round bottom flask with a reflux condenser was placed
extractionextracted with ethyl acetate (3×50 mL)
dry with materialThe organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customPurified

Sources & evidence

ORD record: ord-1b210025c3884fd1a7e299de7a2415e2
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935699B2

Reaction notes

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