Iodine → (E,E)-N-(2-Methylpropyl)-2,4-decadienamide

HRID 1455628Notes

Reaction equation

HRID 1455628 reaction equation
[CH2:1]([NH:5][C:6](=[O:16])/[CH:7]=[CH:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:2]([CH3:4])[CH3:3].II>C1(C)C=CC=CC=1>[CH2:1]([NH:5][C:6](=[O:16])/[CH:7]=[CH:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 807IodineHCID 11368078pellitorine

Product 1

HCID 5318516(E,E)-N-(2-Methylpropyl)-2,4-decadienamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

277 mg of 2E,4Z-decadienoic acid-N-isobutylamide from Example 1 were stirred with 29 mg of iodine in 10 ml of toluene for one hour at room temperature. The mixture was chromatographed on silica gel 60 with the eluent hexane/ethyl acetate 5:1. Yield: 61 mg (>95%, NMR); 1H-NMR (CDCl3; 200 MHz): 7.19 (1H, dd, 14.9 Hz, 9.7 Hz), 6.13 (1H, dd, 15.1 Hz, 9.6 Hz), 6.07 (1H, dd, 15.1 Hz, 6.4 Hz), 5.75 (1H, d 14.9 Hz), 5.50 (1H, bs), 3.17 (2H, dd, 6.9 Hz, 6.1 Hz), 2.14 (2H, dd, 7 Hz, 6.4 Hz), 1.80 (1H, m, 6.7 Hz), 1.42 (2H, m, 7.1 Hz), 1.37-1.22 (4H, m), 0.93 (6H, d, 6.7 Hz), 0.89 (3H, m) ppm.

Workup

  1. customThe mixture was chromatographed on silica gel 60 with the eluent hexane/ethyl acetate 5:1

Sources & evidence

ORD record
ord-db6c8ee5d02b4d68b9a75dd0787a49b6
Source dataset
uspto-grants-2009_01
Patent number
US07482479B2

Reaction notes

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