Hydrochloric Acid → tert-butyl (2E)-3-(pyridin-3-yl)prop-2-enoate

HRID 496065

Reaction equation

HRID 496065 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])[CH:3]=1.[C:13]([O-])([CH3:16])([CH3:15])[CH3:14].[K+]>CCOCC.O1CCCC1>[N:2]1[CH:7]=[CH:6][CH:5]=[C:4](/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 776396trans-3-(3-Pyridyl)acrylic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 11030960tert-butyl (2E)-3-(pyridin-3-yl)prop-2-enoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

Ethereal HCl is added to a solution of 45 g of (2E)-3-(3-pyridyl)-2-propenoic acid in 300 ml of ether until the pH is acid. The precipitate obtained is filtered off, washed with ether and dried under reduced pressure. The product is then taken up in 600 ml of thionyl chloride and heated at reflux for 2 hours, and is then concentrated under reduced pressure and taken up successively in toluene and then ether. The residue obtained is then diluted with 1 liter of tetrahydrofuran, stirred at 5° C., and 67 g of potassium tert-butanolate in 2.5 liters of tetrahydrofuran are added. After reacting for 3 hours at 5° C. and for 1 hour at 20° C., the reaction mixture is subjected to customary treatment, allowing the expected product to be obtained after evaporation under reduced pressure.

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered off
  3. washwashed with ether
  4. customdried under reduced pressure
  5. temperatureheated
  6. temperatureat reflux for 2 hours
  7. concentrationis then concentrated under reduced pressure
  8. customThe residue obtained

Sources & evidence

ORD record
ord-09b9d996eec544dc8cbbb81bddfb0d35
Source dataset
uspto-grants-2005_09
Patent number
US06943184B2

Linked notes

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