Methanol → (6-((2,4-Dichlorobenzyl)oxy)-1,1-dioxido-1-benzothiophen-3-yl)acetic acid

HRID 591474Notes

Reaction equation

C([O:3][C:4](=[O:27])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[CH:14][C:9]=2[S:8](=[O:26])(=[O:25])[CH:7]=1)C.C1COCC1.CO.O.[OH-].[Li+]>O>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:13]1[CH:12]=[CH:11][C:10]2[C:6]([CH2:5][C:4]([OH:27])=[O:3])=[CH:7][S:8](=[O:26])(=[O:25])[C:9]=2[CH:14]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a mixture of ethyl(6-((2,4-dichlorobenzyl)oxy)-1,1-dioxido-1-benzothiophen-3-yl)acetate (8.00 g), THF (64 mL), MeOH (64 mL) and H2O (32 mL) was added lithium hydroxide hydrate (1.58 g) and the resulting mixture was stirred at 25° C. for 16 h. The solvent was removed under reduced pressure. The residue was suspended in water, and the mixture was acidified by 6N HCl. The resulting solid was collected by filtration, and dried under reduced pressure to give the title compound (4.00 g).

Workup

customThe solvent was removed under reduced pressure
filtrationThe resulting solid was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-cd8669838b1341c8aef62b44d3132c90
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238639B2

Reaction notes

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