Hydrochloric Acid → HCID 57542005, compound

HRID 2422230Notes

Reaction equation

HRID 2422230 reaction equation
[Cl:1][C:2]1[C:3]2[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=2[S:5][C:6]=1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:11][CH:10]=1.O1CCCC1.O.[OH-].[Li+].Cl>O.CO>[Cl:1][C:2]1[C:3]2[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=2[S:5][C:6]=1[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 57541978HCID 57541978, compound

Product 1

HCID 57542005HCID 57542005, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 4-[(3-chlorobenzo[b]thien-2-yl) methoxy]benzenepropanoate (1.5 g, 4.0 mmol), tetrahydrofuran (20 mL), methanol (5 mL), water (2 mL) and lithium hydroxide monohydrate (0.34 g, 8.0 mmol) was stirred overnight at room temperature. The reaction mixture was neutralized with 0.5N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3:1) to give the title compound (1.3 g, yield 94%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-3ba9937a05ba4621aa0e36e386e1f21f
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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