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

HRID 2228202Notes

Reaction equation

HRID 2228202 reaction equation
[F:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:19][CH2:18][CH2:17][C:16]([C:20]([O:22]CC)=[O:21])=[CH:15][C:14]=3[CH:25]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>O1CCCC1CCO>[F:27][C:2]([F:1])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:19][CH2:18][CH2:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][C:14]=3[CH:25]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18472320Ethyl 7-(4-trifluoromethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate

Product 1

HCID 184724787-(4-Trifluoromethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

To a solution of ethyl 7—(4-trifluoromethoxy-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (323.9 mg) in tetrahydrofuran-ethanol (5-5 ml) was added 1N sodium hydroxide (2.0 ml) at room temperature, and the mixture was stirred for 5 days and concentrated under reduced pressure. To the residue 1N hydrochloric acid (5 ml) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated. The resulting crystal was collected by filtration to give 7—(4-trifluoromethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (282 mg) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue 1N hydrochloric acid (5 ml) was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. filtrationThe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-acb846037d654cb2806462a030792adf
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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