Reaktionsgleichung
[Cl:1][C:2]1[C:7]2[CH2:8][CH:9]([C:10]([OH:12])=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:13]([NH:20][CH2:21]/[C:22](/[CH3:25])=[CH:23]/[CH3:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.[O-]P1(OP([O-])(=O)OP([O-])(=O)OP([O-])(=O)O1)=O.[Na+].[Na+].[Na+].[Na+].C(OCC)(=O)C>C(Cl)Cl>[CH2:13]([N:20]([CH2:21]/[C:22](/[CH3:25])=[CH:23]/[CH3:24])[C:10]([CH:9]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=2[CH2:8]1)=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
3-Chloro-1,2-dihydrocyclobutabenzene-1-carboxylic acid (3.78 mmol, 690 mg) was dissolved in DCM (10 ml). (E)-N-benzyl-2-methylbut-2-en-1-amine (5.67 mmol, 993 mg) and triethylamine (7.56 mmol, 1.050 ml, 765 mg) were added, followed by cyclophos 50% in ethyl acetate (4.53 mmol, 2.70 ml, 2886 mg). The reaction mixture was stirred overnight at room temperature and then diluted with DCM (5 ml) and washed in turn with 2 N HCl (10 ml), 2 N NaOH (10 ml) and brine (10 ml). The organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a crude residue that was purified by silica column chromatography (eluting with heptane—50% ethyl acetate:heptane) to give (E)-N-benzyl-3-chloro-N-(2-methylbut-2-enyl)-1,2-dihydrocyclobutabenzene-1-carboxamide (430 mg). m/z: 340.5 [M+H]+.
Aufarbeitung
- washwashed in turn with 2 N HCl (10 ml), 2 N NaOH (10 ml) and brine (10 ml)
- dry with materialThe organic extracts were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give a crude residue that
- customwas purified by silica column chromatography (eluting with heptane—50% ethyl acetate:heptane)
Quellen und Nachweise
- ORD-Eintrag
- ord-f424aff4570c44c8a5fd09da6be53fea
- Quelldatensatz
- uspto-grants-2014_05
- Patentnummer
- US08729274B2
Verknüpfte Notizen
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