Lithium hydroxide, monohydrate → [6-Fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid

HRID 1644722Notes

Reaction equation

HRID 1644722 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][C:6]1[CH:15]=[C:14]([C:16](=[O:27])[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:28])[CH:12]=2)[CH:7]=1)C.O.[OH-].[Li+]>O1CCCC1.O>[F:28][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([CH2:5][C:4]([OH:29])=[O:3])[CH:15]=[C:14]2[C:16](=[O:27])[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:24])=[O:25])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59350811[6-Fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester

Product 1

HCID 46204884[6-Fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acidYield 90.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [6-fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester (0.63 g, 1.52 mmol) in tetrahydrofuran (6 mL) and water (6 mL) was added lithium hydroxide monohydrate (0.83 g, 1.98 mmol). The reaction mixture was heated at reflux for 3 hours. After cooling to room temperature, more water was added, and tetrahydrofuran was removed under reduced pressure. The pH was adjusted to 2 with ca. 2 mL of 4 N hydrochloric acid. The resulting light tan solid was collected by filtration to give pure [6-fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid (0.53 g, 90%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. customtetrahydrofuran was removed under reduced pressure
  4. filtrationThe resulting light tan solid was collected by filtration

Sources & evidence

ORD record
ord-fc8bc5a25e154c7391f3950590752e1e
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

Loading…