Cyclohexyl bromide → N-cyclohexyloxyphthalimide

HRID 29168

Reaktionsgleichung

[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[CH2:13]1[CH2:23][CH2:22]N2[C:16](=NCCC2)[CH2:15][CH2:14]1.C1(Br)CCCCC1>CN(C=O)C>[CH:13]1([O:1][N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[CH2:14][CH2:15][CH2:16][CH2:22][CH2:23]1

Komponenten

Reaktionsbedingungen

Temperatur: 55 °C

Versuchsvorschrift

N-hydroxylphthalimide (61.3 mmol, 10.0 g) was dissolved in anhydrous DMF (60 mL) under nitrogen. To the stirring solution, DBU (92.0 mmol, 13.75 mL) was injected followed by cyclohexyl bromide (76.6 mmol, 9.43 mL) and the reaction was warmed to 55° C. After stirring for 15 hours, the reaction was warmed to 80° C. for 5 hours, then cooled to room temperature and concentrated to a red oil. The reaction was partitioned between ethyl acetate and 1N HCl. The organic layer was washed with 1N NaOH, brine and dried over magnesium sulfate. The solvent was removed under vacuum and the crude product was triturated with hexanes providing 2.89 g (19%) of a yellow solid. Rf: 0.7 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.80 (2H,m), 7.73(2H,m), 4.21 (1H,m), 2.02-1.98 (2H,m), 1.87-1.82 (2H,m), 1.59-1.53 (4H,m), 1.30-1.24 (2H,m).

Aufarbeitung

temperaturethe reaction was warmed to 80° C. for 5 hours
temperaturecooled to room temperature
concentrationconcentrated to a red oil
customThe reaction was partitioned between ethyl acetate and 1N HCl
washThe organic layer was washed with 1N NaOH, brine
dry with materialdried over magnesium sulfate
customThe solvent was removed under vacuum
customthe crude product was triturated with hexanes providing 2.89 g (19%) of a yellow solid

Quellen und Nachweise

ORD-Eintrag: ord-16dd12d525704f8bb2157302ec748a15
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07419967B2

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