Sodium Hydroxide → 2-[2-Ethyl-4-(p-tolyl)-5,6,7,8-tetrahydrobenzothiopheno[2,3-b]pyridin-3-yl]pentanoic acid

HRID 1627907Notes

Reaction equation

[CH2:1]([C:3]1[N:8]=[C:7]2[S:9][C:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[C:6]2=[C:5]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[C:4]=1[CH:23]([CH2:29][CH2:30][CH3:31])[C:24]([O:26]CC)=[O:25])[CH3:2].[OH-].[Na+]>CO.C(O)C>[CH2:1]([C:3]1[N:8]=[C:7]2[S:9][C:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[C:6]2=[C:5]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[C:4]=1[CH:23]([CH2:29][CH2:30][CH3:31])[C:24]([OH:26])=[O:25])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of ethyl 2-[2-ethyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]pentanoate (0.322 g; 0.739 mmol) in a mixture methanol-ethanol (2:1) (22.5 mL) was added a solution of sodium hydroxide 5% (18 mL; 22.5 mmol) and the reaction mixture was heated at 90° C. for 4 h. The organic volatiles were removed under reduced pressure and the remaining basic solution was acidified until pH 2 with a solution of hydrochloric acid 1N. The aqueous layer was extracted with ethyl acetate, the organics were combined, dried over sodium sulphate and concentrated under reduced pressure to furnish 0.203 g (68%) of the title compound as a white solid.

Workup

customThe organic volatiles were removed under reduced pressure
extractionThe aqueous layer was extracted with ethyl acetate
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-7a8f274bfb8a41bd8a699e674ed1c326
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785638B2

Reaction notes

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