Tetrahydrofuran → 7-(4-Fluorophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid

HRID 566096Notes

Reaction equation

HRID 566096 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][C:14]([C:18]([O:20]C)=[O:19])=[CH:13][C:12]=3[CH:22]=2)=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][C:14]([C:18]([OH:20])=[O:19])=[CH:13][C:12]=3[CH:22]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18472577HCID 18472577, compound

Product 1

HCID 184722877-(4-Fluorophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To methyl 7-(4-fluorophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (0.27 g) were added THF (5.0 ml), ethanol (10.0 ml) and 2N sodium hydroxide solution (1.0 ml), and the mixture was stirred at room temperature for 19 hours. Under reduced pressure, the solvent was removed, and the residue was diluted with water (100 ml). The aqueous layer was made acidic with hydrochloric acid, and the mixture was extracted with ethyl acetate (100 ml). The organic layer was dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was crystallized and washed with hexane to give 7-(4-fluorophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (0.22 g, 86%) as white crystals.

Workup

  1. customUnder reduced pressure, the solvent was removed
  2. additionthe residue was diluted with water (100 ml)
  3. extractionthe mixture was extracted with ethyl acetate (100 ml)
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was crystallized
  7. washwashed with hexane

Sources & evidence

ORD record
ord-06fa9c6e618843c6918d89ac531f5d7f
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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