Lithium hydroxide, monohydrate → 5-Phenylbenzo[b]thiophene-2-carboxylic acid

HRID 403294Notes

Reaction equation

HRID 403294 reaction equation
[C:1]1([C:7]2[CH:19]=[CH:18][C:10]3[S:11][C:12]([C:14]([O:16]C)=[O:15])=[CH:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[Li].O>C1COCC1.O>[C:1]1([C:7]2[CH:19]=[CH:18][C:10]3[S:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 19007392Methyl 5-phenylbenzo[b]thiophene-2-carboxylate

Product 1

HCID 596260715-Phenylbenzo[b]thiophene-2-carboxylic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of compound 13b (510 mg, 1.9 mmol) and LiOH.H2O (319 mg, 7.6 mmol) in THF/H2O (10/10 mL) was stirred at room temperature overnight. The resulting mixture was concentrated and diluted with water. The water layer was acidified with 1N aqueous HCl to pH˜4 and extracted with CH2Cl2. The organic solution was dried over Na2SO4 and concentrated to give compound 13c (479 mg), which was used in the next reaction without further purification. MS m/z (M+H+) 255.0.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-05e210887de8459a811d173e5461b2d1
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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