HCID 67867952, compound → HCID 53661494, compound

HRID 2232715Notes

Reaction equation

HRID 2232715 reaction equation
C([O:3][C:4](=[O:16])[CH:5]([CH3:15])[CH2:6][CH:7]=[CH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)C>[OH-].[Na+].CO>[CH3:15][CH:5]([CH2:6][CH:7]=[CH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[C:4]([OH:16])=[O:3]

Participants

4

Reactant 1

HCID 67867952HCID 67867952, compound

Product 1

HCID 53661494HCID 53661494, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 9.95 g of (R,S)-Z]-2-methyl-5-(3-pyridinyl)-4-pentenoic acid ethyl ester in 75 mL of 1N NaOH and 75 mL of methanol were stirred at reflux for 3 hours, then most of the methanol was removed under reduced pressure. After the solution was extracted with dichloromethane (3×50 mL). the aqueous layer was neutralized with 75 ml of 1N HCl and extracted with dichloromethane (4×40 mL). The dried (Na2SO4) extracts were evaporated to give 7.28 g of a solid which was crystallized from ether-hexane to yield 6.12 g of [(R,S)-Z]-2-methyl-5-(3-pyridinyl)-4-pentenoic acid, mp 79°-82° C.

Workup

  1. temperatureat reflux for 3 hours
  2. custommost of the methanol was removed under reduced pressure
  3. extractionAfter the solution was extracted with dichloromethane (3×50 mL)
  4. extractionextracted with dichloromethane (4×40 mL)
  5. dry with materialThe dried (Na2SO4) extracts
  6. customwere evaporated

Sources & evidence

ORD record
ord-21b8198ac05a4c2b8d8f2173a0e8e884
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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