Sodium Hydroxide → 5-Carboxy-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene

HRID 9879

Reaction equation

C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[C:8]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[CH:7]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([C:6]1[S:10][C:9]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)=[C:8]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[CH:7]=1)([OH:5])=[O:3]

Participants

Conditions

Temperature: 100 °C

Procedure

5-Ethoxycarbonyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene (15.17 g (46.3 mmol), prepared as described in 1)) was dissolved in ethanol (150 ml). To the solution was added an aqueous solution of 1 N sodium hydroxide (93 ml, 93 mmol), and the resulting mixture was stirred at 100° C. for 30 minutes. At the end of this time, ethanol was removed by distillation under reduced pressure. To the reaction residue was added water, and then an aqueous solution of 1 N hydrochloric acid (93 ml). The precipitated crystals were collected by filtration, to give the title compound (12.64 g) as a pale brown powder (yield 91%).

Workup

customAt the end of this time, ethanol was removed by distillation under reduced pressure
additionTo the reaction residue was added water
filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-d7ef2be036f64ada85c82b1e0ea6db93
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091352B2

Linked notes

Loading…