Tetrahydrofuran → 7-(4-Ethoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylic acid

HRID 1978666Notes

Reaction equation

HRID 1978666 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[S:19][CH2:18][CH2:17][C:16]([C:20]([O:22]C)=[O:21])=[CH:15][C:14]=3[CH:24]=2)=[CH:6][CH:5]=1)[CH3:2].C1COCC1.[OH-].[Na+]>CO>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[S:19][CH2:18][CH2:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][C:14]=3[CH:24]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21995712Methyl 7-(4-ethoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate

Product 1

HCID 219957917-(4-Ethoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylic acidYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 7-(4-ethoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate (960 mg) were added THF (19.2 ml), methanol (9.6 ml) and 1N sodium hydroxide (3.4 ml), and the mixture was stirred at room temperature for 3 hours. Under reduced pressure, the organic solvent was evaporated. To the residue was added ethyl acetate, and the mixture was extracted with water. To the mixture was added 6N hydrochloric acid (2 ml), and the mixture was extracted with ethyl acetate/THF, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 7-(4-ethoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylic acid (850 mg).

Workup

  1. customUnder reduced pressure, the organic solvent was evaporated
  2. additionTo the residue was added ethyl acetate
  3. extractionthe mixture was extracted with water
  4. additionTo the mixture was added 6N hydrochloric acid (2 ml)
  5. extractionthe mixture was extracted with ethyl acetate/THF
  6. washwashed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-6903dc053735435099141c6f4315dc4b
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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