Triethylamine → 4-Ethyl-2,4-hexadien-1-yl 3-pyridinecarboxylate

HRID 2396891Notes

Reaction equation

HRID 2396891 reaction equation
[CH2:1](/[C:3](=[CH:8]\[CH3:9])/[CH:4]=[CH:5]/[CH2:6][OH:7])[CH3:2].C(N(CC)CC)C.Cl.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1>ClCCl>[N:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([O:7][CH2:6][CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][CH3:9])=[O:25])[CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 86749292(E,E)-4-ethyl-2,4-hexadien-1-ol

Product 1

HCID 542720204-Ethyl-2,4-hexadien-1-yl 3-pyridinecarboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (E,E)-4-ethyl-2,4-hexadien-1-ol (2.0 g), triethylamine (8 ml), and dichloromethane (15 ml) at 0° C. was added nicotinic acid chloride hydrochloride (4.23 g). The solution was stirred at 0° C. for 1.5 hours and at room temperature for 14 hours. The reaction mixture was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (chloroform) to give 4-ethyl-2,4-hexadien-1-yl 3-pyridinecarboxylate (3.3 g) as an oil.

Workup

  1. washThe reaction mixture was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel (chloroform)

Sources & evidence

ORD record
ord-3dda286a48a1400c87869b1a631edc4e
Source dataset
uspto-grants-1996_02
Patent number
US05495023

Reaction notes

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