Lithium Hydroxide → 2-(3-((6-(3-Fluorophenyl)-2,3-dihydro-1H-inden-1-yl)oxy)phenoxy)acetic acid

HRID 1051108Notes

Reaction equation

[OH-].[Li+].[F:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:18]=[C:17]3[C:13]([CH2:14][CH2:15][CH:16]3[O:19][C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=3)[O:23][CH2:24][C:25]([O:27]C)=[O:26])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:18]=[C:17]3[C:13]([CH2:14][CH2:15][CH:16]3[O:19][C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=3)[O:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Aqueous lithium hydroxide (1 N, 1 mL, 1 mmol) was added to a solution of methyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)oxy)phenoxy)acetate (38 mg, 0.091 mmol) in THF (1 mL) in a scintillation vial. The vial was sealed and stirred overnight at 40° C. After 24 h, the reaction mixture was allowed to cool and the volatiles were concentrated. The residue was acidified with hydrochloric acid (1 N, 1 mL) and extracted with ethyl acetate (3×2 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by preparative TLC (1000 mm thickness, 15% methanol/dichloromethane) to afford 21 mg (61%) of the title compound.

Workup

customThe vial was sealed
waitAfter 24 h
temperatureto cool
concentrationthe volatiles were concentrated
extractionextracted with ethyl acetate (3×2 mL)
dry with materialThe combined organic extracts were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe resulting crude residue was purified by preparative TLC (1000 mm thickness, 15% methanol/dichloromethane)

Sources & evidence

ORD record: ord-56150c8200ed4d9db1661d223bc6f013
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388153B2

Reaction notes

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