(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
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]12Participants
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
- stirringby stirring at 60° C. for an additional hour
- customInsoluble matters were separated by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed successively with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by means of silica gel chromatography (
- 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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