(2E,6E,10E,14E,18E,22E,26E,30E)-1-Bromo-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaene → Phthalimide

HRID 2286349Notes

Reaction equation

HRID 2286349 reaction equation
CC(C)=CCC/C(/C)=C/CC/C(/C)=C/CC/C(/C)=C/CC/C(/C)=C/CC/C(/C)=C/CC/C(/C)=C/CC/C(/C)=C/CC/C(/C)=C/CBr.[C:47]1(=[O:57])[NH:51][C:50](=[O:52])[C:49]2=[CH:53][CH:54]=[CH:55][CH:56]=[C:48]12.[K]>CN(C)C=O>[C:47]1(=[O:57])[NH:51][C:50](=[O:52])[C:49]2=[CH:53][CH:54]=[CH:55][CH:56]=[C:48]12

Participants

4

Procedure

A mixture comprising 17.4 g of solanesyl bromide, 5.6 g of potassium phthalimide and 70 ml of N,N-dimethylformamide was stirred for 2 hours, followed by stirring at 60° C. for an additional hour. Insoluble matters were separated by filtration, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed successively with water and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by means of silica gel chromatography (eluted with a mixture of n-hexane and benzene) to obtain 12,8 g of N-solanesyl phthalimide (yield, 67%, m.p., 51°-53° C.).

Workup

  1. stirringby stirring at 60° C. for an additional hour
  2. customInsoluble matters were separated by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed successively with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by means of silica gel chromatography (
  9. washeluted with a mixture of n-hexane and benzene)

Sources & evidence

ORD record
ord-ca9c9ed8b8834fa2bc5840adb39a66fe
Source dataset
uspto-grants-1981_05
Patent number
US04265910

Reaction notes

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