Ethyl isocyanate → (E,E)-4-ethyl-2,4-hexadien-1-yl ethylcarbamate

HRID 2396893Notes

Reaction equation

HRID 2396893 reaction equation
[CH2:1](/[C:3](=[CH:8]\[CH3:9])/[CH:4]=[CH:5]/[CH2:6][OH:7])[CH3:2].[CH2:10]([N:12]=[C:13]=[O:14])[CH3:11]>ClCCCl>[CH2:10]([NH:12][C:13](=[O:14])[O:7][CH2:6]/[CH:5]=[CH:4]/[C:3](/[CH2:1][CH3:2])=[CH:8]/[CH3:9])[CH3:11]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 86749292(E,E)-4-ethyl-2,4-hexadien-1-ol

Product 1

HCID 86749293(E,E)-4-ethyl-2,4-hexadien-1-yl ethylcarbamateYield 80%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of (E,E)-4-ethyl-2,4-hexadien-1-ol (2.0 g) and ethyl isocyanate (1.13 g) in 1,2-dichloroethane (12 ml) was stirred at 0° C. for 3 hours and at room temperature for 12 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 (E,E)-4-ethyl-2,4-hexadien-1-yl ethylcarbamate (2.5 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-e6ce32a91486475c97142ca524bfa2d8
Source dataset
uspto-grants-1996_02
Patent number
US05495023

Reaction notes

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