Trifluoroacetic acid → 4-Ethyl-2,4-hexadien-1-yl carbamate

HRID 2396892Notes

Reaction equation

HRID 2396892 reaction equation
[CH2:1](/[C:3](=[CH:8]\[CH3:9])/[CH:4]=[CH:5]/[CH2:6][OH:7])[CH3:2].[O-:10][C:11]#[N:12].[Na+].FC(F)(F)C(O)=O>C1C=CC=CC=1>[C:11](=[O:10])([O:7][CH2:6][CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][CH3:9])[NH2:12]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 517096Sodium CyanateHCID 86749292(E,E)-4-ethyl-2,4-hexadien-1-ol

Product 1

HCID 540257994-Ethyl-2,4-hexadien-1-yl carbamateYield 49.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of (E,E)-4-ethyl-2,4-hexadien-1-ol (3.0 g), sodium cyanate (3.1 g), and benzene (15 ml) at room temperature was added dropwise trifluoroacetic acid (5.42 g) during 1 hour. After being stirred for 2 hours at the same temperature, the reaction mixture was partitioned between water and ethyl acetate. The organic layer separated was washed with aqueous sodium bicarbonate, water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (1% methanol-dichloromethane) to give 2.0 g of 4-ethyl-2,4-hexadien-1-yl carbamate.

Workup

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. customThe organic layer separated
  3. washwas washed with aqueous sodium bicarbonate, water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel (1% methanol-dichloromethane)

Sources & evidence

ORD record
ord-ebb38c1fdefb4018a8f43d8101e4d402
Source dataset
uspto-grants-1996_02
Patent number
US05495023

Reaction notes

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