Farnesyl bromide → 2-(3,7,11-Trimethyl-2,6,10-dodecatrienyl)-1H-isoindole-1,3(2H)-dione

HRID 327901Notes

Reaction equation

HRID 327901 reaction equation
[CH2:1](Br)[CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:4].[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>CN(C)C=O>[CH3:4][C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:2][CH2:1][N:21]1[C:17](=[O:27])[C:18]2[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:20]1=[O:22]

Participants

4

Reactant 2

HCID 550199Farnesyl bromideHCID 24194345Phthalimide potassium salt

Product 1

HCID 542051882-(3,7,11-Trimethyl-2,6,10-dodecatrienyl)-1H-isoindole-1,3(2H)-dioneYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.47 g of the above farnesyl bromide in 20 ml of dry dimethyformamide (DMF) at room temperature under argon was treated with 1.83 g (9.9 mmol, 1.1 eq.) of potassium phthalimide and stirred for 3 hours at room temperature. The solvent was removed under reduced pressure, the residue was triturated with 150 ml of ethyl ether, and the precipitate was filtered off. The ethereal solution was washed with 50 ml of H2O and 50 ml of brine, dried over MgSO4 and evaporated to yield 2.96 g of crude title compound as a milky oil. Purification by flash chromatography on 300 g of Merck 9385 silica, eluted with 7:93 ethyl acetate:petroleum ether afforded 2.56 g (81%) of the desired product as a colorless oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was triturated with 150 ml of ethyl ether
  3. filtrationthe precipitate was filtered off
  4. washThe ethereal solution was washed with 50 ml of H2O and 50 ml of brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customto yield 2.96 g of crude title compound as a milky oil
  8. customPurification by flash chromatography on 300 g of Merck 9385 silica
  9. washeluted with 7:93 ethyl acetate

Sources & evidence

ORD record
ord-7d755848ecdf47aca97349e48f8e99d6
Source dataset
uspto-grants-1993_12
Patent number
US05273969

Reaction notes

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