Lithium Hydroxide → 3-(2-(4-(3-(2,6-Dichloro-phenyl)-5-isopropyl-3-H-(1,2,3)triazol-4ylmethyoxy)-2-methyl-phenyl)-vinyl)-benzoic acid

HRID 424827Notes

Reaction equation

HRID 424827 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[N:21]([C:28]4[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=4[Cl:35])[N:22]=[N:23][C:24]=3[CH:25]([CH3:27])[CH3:26])=[CH:14][C:13]=2[CH3:36])[CH:5]=1.[OH-].[Li+].CCCCCC.C(OCC)(=O)C>C1COCC1>[Cl:35][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([Cl:34])[C:28]=1[N:21]1[C:20]([CH2:19][O:18][C:15]2[CH:16]=[CH:17][C:12]([CH:11]=[CH:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:37])=[O:2])=[C:13]([CH3:36])[CH:14]=2)=[C:24]([CH:25]([CH3:27])[CH3:26])[N:23]=[N:22]1

Participants

5

Reactant 3

HCID 3939Lithium Hydroxide2×HCID 21226206Ethyl acetate hexaneHCID 1317294223-(2-(4-(3-(2,6-Dichloro-phenyl)-5-isopropyl-3-H-(1,2,3)triazol-4ylmethyoxy)-2-methyl-phenyl)-vinyl)-benzoic acid methyl ester

Product 1

HCID 765839163-(2-(4-(3-(2,6-Dichloro-phenyl)-5-isopropyl-3-H-(1,2,3)triazol-4ylmethyoxy)-2-methyl-phenyl)-vinyl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 3-(2-(4-(3-(2,6-dichloro-phenyl)-5-isopropyl-3-H-(1,2,3)triazol-4ylmethyoxy)-2-methyl-phenyl)-vinyl)-benzoic acid methyl ester (0.025 g, 0.046 mmol) in THF (3 mL) is added lithium hydroxide (0.005 g, 0.21 mmol). The reaction mixture is heated to 55° C. The reaction is determined to be incomplete due to the presence of starting material by TLC (1:1 hexane/ethyl acetate). An additional amount of lithium hydroxide (0.050 g) is added and the reaction is heated to 60° C. for 3 h. The reaction is quenched with aqueous 1 N HCl and is extracted with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound. ES/MS m/e 521.8 (M+1).

Workup

  1. temperaturethe reaction is heated to 60° C. for 3 h
  2. customThe reaction is quenched with aqueous 1 N HCl
  3. extractionis extracted with ethyl acetate
  4. washThe organic layer is washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-16df141573514905aaa0e45e5679f1ad
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

Loading…