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

HRID 2294995Notes

Reaction equation

HRID 2294995 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-5213ebd6c2d742a3bf9f9c8d9cab435e
Source dataset
uspto-grants-1997_11
Patent number
US05691366

Reaction notes

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