Sodium Hydroxide → 7-(5-Methyl-2-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid

HRID 566090Notes

Reaction equation

HRID 566090 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:16][CH2:15][CH2:14][C:13]([C:17]([O:19]C)=[O:18])=[CH:12][C:11]=3[CH:21]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:16][CH2:15][CH2:14][C:13]([C:17]([OH:19])=[O:18])=[CH:12][C:11]=3[CH:21]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18472362Methyl 7-(5-methyl-2-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylate

Product 1

HCID 184726407-(5-Methyl-2-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acidYield 81.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In THF (10.5 ml) and methanol (5.2 ml) was dissolved methyl 7-(5-methyl-2-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (525 mg), and to the mixture was added 1N sodium hydroxide (10.5 ml). The mixture was stirred at room temperature for 2 hours. Under reduced pressure, the organic solvent was removed, and to the residue was added ethyl acetate. The mixture was extracted with water, and to the aqueous layer was added 6N hydrochloric acid to make the solution pH 4-5, which was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was removed to give 7-(5-methyl-2-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (410 mg).

Workup

  1. customUnder reduced pressure, the organic solvent was removed
  2. additionto the residue was added ethyl acetate
  3. extractionThe mixture was extracted with water
  4. additionto the aqueous layer was added 6N hydrochloric acid
  5. extractionwas extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. customUnder reduced pressure, the solvent was removed

Sources & evidence

ORD record
ord-94f5330871154f1dbc294775fc000c0a
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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