2-(1-Benzo[b]thiophen-2-yl-1-methylethyl)-4-methoxy-benzoic acid → HCID 66835213, compound

HRID 61866Notes

Reaction equation

[S:1]1[C:5]([C:6]([C:9]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)([CH3:8])[CH3:7])=[CH:4][C:3]2[CH:20]=[CH:21][CH:22]=[CH:23][C:2]1=2>O>[CH3:19][O:18][C:16]1[CH:17]=[C:9]2[C:10](=[CH:14][CH:15]=1)[C:11](=[O:13])[C:4]1[C:3]3[CH:20]=[CH:21][CH:22]=[CH:23][C:2]=3[S:1][C:5]=1[C:6]2([CH3:7])[CH3:8]

Participants

Conditions

Temperature: 100 °C

Procedure

To 2-(1-benzo[b]thiophen-2-yl-1-methylethyl)-4-methoxy-benzoic acid (Compound Z4, 68 mg, 0.22 mmol), polyphosphoric acid (3.5 g) was added, and the mixture was stirred for 1 hr at 100° C. under heating. The mixture was added with water, extracted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate. The residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (41 mg, 63%).

Workup

temperatureunder heating
extractionextracted with ethyl acetate
washwashed with water
dry with materialThe organic layer was dried over magnesium sulfate
customThe residues obtained
concentrationafter concentration under reduced pressure
customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-6bbfad9e6b2844568b529556b7db471e
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Reaction notes

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