Hydrochloric Acid → HCID 68842177, compound

HRID 238890Notes

Reaction equation

HRID 238890 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[CH:11][S:10][C:9]=2[C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)=[O:4].[Li+].[OH-].Cl>O1CCOCC1.C(OCC)(=O)C>[F:24][C:22]([F:23])([F:25])[C:19]1[CH:20]=[CH:21][C:16]([CH2:15][O:14][C:13]2[C:9]3[S:10][CH:11]=[CH:12][C:8]=3[CH:7]=[CH:6][C:5]=2[C:3]([OH:4])=[O:2])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68840106HCID 68840106, compound

Product 1

HCID 68842177HCID 68842177, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

323 mg 7-(4-Trifluoromethyl-benzyloxy)-benzo[b]thiophene-6-carboxylic acid methyl ester was dissolved in 10 ml of 1,4-dioxane. To this was added 4.4 ml of 1 M LiOH (aq), and the reaction was stirred for 7 h at 60° C. and overnight at room temperature. The reaction mixture was diluted with 5 ml of ethyl acetate, acidified to pH 3 with 2N HCl (aq) and extracted with 10 ml ethyl acetate 4 times. The combined organic layers were washed with brine, dried over sodium sulphate and concentrated in vacuo to give 271 mg of 7-(4-trifluoromethyl-benzyloxy)-benzo[b]thiophene-6-carboxylic acid.

Workup

  1. extractionextracted with 10 ml ethyl acetate 4 times
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68206b8b54ad46e1ae27828d974be3e8
Source dataset
uspto-grants-2014_02
Patent number
US08642643B2

Reaction notes

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