Lithium hydroxide, monohydrate → 3-Methyl 5-[3(2-quinolinylmethyloxy)-benzyloxy]benzo(b)thiophene-2-carboxylic acid

HRID 2248905Notes

Reaction equation

HRID 2248905 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]4[CH:33]=[CH:32][C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]=4)[CH:17]=3)=[CH:13][C:7]=2[C:6]=1[CH3:34])=[O:4].O.[OH-].[Li+]>C1COCC1.CO.O>[CH3:34][C:6]1[C:7]2[CH:13]=[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]4[CH:33]=[CH:32][C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]=4)[CH:17]=3)[CH:11]=[CH:10][C:8]=2[S:9][C:5]=1[C:3]([OH:4])=[O:2]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 54370568Methyl-3-methyl-5-[3-(2quinolinylmethyloxy)benzyloxy]benzo(b)thiophene-2-carboxylate

Product 1

HCID 149952903-Methyl 5-[3(2-quinolinylmethyloxy)-benzyloxy]benzo(b)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl-3-methyl-5-[3-(2quinolinylmethyloxy)benzyloxy]benzo(b)thiophene-2-carboxylate (355 mg, 0.76 mmol) in THF (10 ml), methanol (10 ml) and water (10 ml) at room temperature is added lithium hydroxide monohydrate (156 mg, 3.71 mmol). The resulting solution is stirred for 16 hours and concentrated. The residue is suspended in water and washed with ether. The aqueous layer is acidified to pH 3. The precipitated solid is filtered, washed with water and methylene chloride and dried to provide 3-methyl 5-[3(2-quinolinylmethyloxy)-benzyloxy]benzo(b)thiophene -2-carboxylic acid.

Workup

  1. concentrationconcentrated
  2. washwashed with ether
  3. filtrationThe precipitated solid is filtered
  4. washwashed with water and methylene chloride
  5. customdried

Sources & evidence

ORD record
ord-7cea00d4174348b4b4bc0770e03309c0
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

Loading…