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

HRID 2294997Notes

Reaction equation

HRID 2294997 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-93dddf0de3ea4d44842bbb8a78b3c7a2
Source dataset
uspto-grants-1997_11
Patent number
US05691366

Reaction notes

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