Acetic Acid → HCID 69315253, compound

HRID 2116630Notes

Reaction equation

HRID 2116630 reaction equation
C(O[C:4](=[O:18])[CH2:5][CH2:6][C:7]1([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:10][CH2:9][CH2:8]1)C.[H-].[Na+].C(O)(=O)C>O1CCCC1>[O:18]=[C:4]1[CH2:5][CH2:6][C:7]2([CH2:8][CH2:9][CH2:10]2)[CH2:11][CH:12]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 69314799HCID 69314799, compound

Product 1

HCID 69315253HCID 69315253, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

20.6 mmol of 3-[1-(ethoxycarbonylethyl)cyclobutyl]propionic acid ethyl ester in solution in tetrahydrofuran are added at 0° C. to 22.7 mmol of 95% sodium hydride in suspension in 15 ml of tetrahydrofuran. The reaction mixture is refluxed for 4 hours and then 49 ml of acetic acid are added. The tetrahydrofuran is evaporated off and the residue obtained is extracted with ethyl acetate. The combined organic phases are washed, filtered, dried and evaporated to yield an oil, which is subjected to chromatography on silica (eluant: dichloromethane/ethyl acetate 95/5) to yield the expected product.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. customThe tetrahydrofuran is evaporated off
  3. customthe residue obtained
  4. extractionis extracted with ethyl acetate
  5. washThe combined organic phases are washed
  6. filtrationfiltered
  7. customdried
  8. customevaporated
  9. customto yield an oil, which

Sources & evidence

ORD record
ord-da6d27580c8045e7b1c60931fefa48a2
Source dataset
uspto-grants-2008_10
Patent number
US07439263B2

Reaction notes

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