Pyridine → HCID 86740122, compound

HRID 463056Notes

Reaction equation

HRID 463056 reaction equation
O[C:2]([CH:5]([CH2:10][CH2:11][CH2:12]/[CH:13]=[C:14](\[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)/[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:6]([O:8][CH3:9])=[O:7])([CH3:4])[CH3:3].N1C=CC=CC=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:4][C:2]([CH:5]([CH2:10][CH2:11][CH2:12]/[CH:13]=[C:14](\[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)/[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:6]([O:8][CH3:9])=[O:7])=[CH2:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 86740123HCID 86740123, compound

Product 1

HCID 86740122HCID 86740122, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

Methyl (E)-2-(1-hydroxy-1-methylethyl)-7-phenyl-7-(3-pyridyl)-6-heptenoate (0.3 g, 0.89 mmole) was dissolved in dichloromethane (10 ml), and the solution was cooled at -10° C. Thionyl chloirde (0.15 ml) was added to the solution, followed by adding pyridine (0.4 ml) and stirring for 10 minutes under the same reaction conditions. After the completion of the reaction, aqueous sodium hydrogencarbonate (5 ml) was added, and the product was extracted with ethyl acetate. The organic layer was worked up in the usual procedure, and the crude product was chromatographed on silica gel, followed by elution with isopropyl ether:ethyl acetate (1:1) to yield methyl (E)-2-(1-methylethenyl)-7-phenyl-7-(3-pyridyl)-6-heptenoate (5-e) (0.25 g, 70%).

Workup

  1. additionThionyl chloirde (0.15 ml) was added to the solution
  2. additionwas added
  3. extractionthe product was extracted with ethyl acetate
  4. customthe crude product was chromatographed on silica gel
  5. washfollowed by elution with isopropyl ether:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-8cfad3105da34ae8a640b6994daf1499
Source dataset
uspto-grants-1985_05
Patent number
US04518602

Reaction notes

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