Hydrochloric Acid → HCID 86699215, compound

HRID 532596Notes

Reaction equation

HRID 532596 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:9])[CH2:7][CH2:8][C:2]1=2.[H-].[Na+].C(OC(=O)[C:16]1C=CC=[C:18]([F:22])[CH:17]=1)C.Cl.[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1>C(OCC)(=O)C.O>[F:22][C:18]1[CH:27]=[CH:26][C:25]([C:29]([CH:7]2[CH2:8][C:2]3[S:1][CH:5]=[CH:4][C:3]=3[C:6]2=[O:9])=[O:28])=[CH:16][CH:17]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 67975Benzoic acid, 3-fluoro-, ethyl esterHCID 19586324H,5H,6H-cyclopenta[b]thiophen-4-one

Product 1

HCID 86699215HCID 86699215, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 3-Fluoro-benzoic acid ethyl ester, the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(4-Fluoro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (0.56 g, 2.1 mmol) as brown solid in 14% yield.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customThe organic layer was collected
  3. dry with materialdried over MgSO4(s)
  4. concentrationconcentrated under reduced pressure
  5. customThe resultant precipitate was collected
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-014725e0ad5d4b93b59d94c6860e9f65
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

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