Hydrochloric Acid → Ethyl 2,3-dihydro-1-benzothiepine-4-carboxylate

HRID 413584Notes

Reaction equation

HRID 413584 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=O.[H-].[Na+].Cl>O1CCCC1>[S:9]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:1]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10]1.[S:9]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:1]=[C:12]([C:13]([OH:15])=[O:14])[CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 18533389Ethyl 4-(2-formylphenylthio)butyrate

Product 2

HCID 11481719Ethyl 2,3-dihydro-1-benzothiepine-4-carboxylateYield 44%HCID 178242472,3-Dihydro-1-benzothiepine-4-carboxylic acidYield 6.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 4-(2-formylphenylthio)butyrate (537 mg) was dissolved in 6 ml of tetrahydrofuran and a suspension of 60% sodium hydride (102 mg) in 5 ml of tetrahydrofuran was dropped at room temperature. Stirring was conducted at room temperature for 1 hour. The mixture was stirred for 30 minutes under reflux. During cooling in ice, 4 ml of a 1N hydrochloric acid was added. Extraction with 10 ml of ethyl acetate was conducted. The organic layer was washed with 20 ml of water three times. The quantitative analysis by HPLC found 220 mg (Yield 44%) of ethyl 2,3-dihydro-1-benzothiepine-4-carboxylate and 28 mg (Yield 6.4%) of 2,3-dihydro-1-benzothiepine-4-carboxylic acid.

Workup

  1. additionwas dropped at room temperature
  2. stirringThe mixture was stirred for 30 minutes
  3. temperatureunder reflux
  4. temperatureDuring cooling in ice
  5. extractionExtraction with 10 ml of ethyl acetate
  6. washThe organic layer was washed with 20 ml of water three times

Sources & evidence

ORD record
ord-e31508c8d36740e19adee23e301de278
Source dataset
uspto-grants-2003_05
Patent number
US06566535B1

Reaction notes

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