Triphenylphosphine → methyl 2-[(tetrahydropyran-4-yl)oxy]-6,7-dihydro-5H-benzocycloheptene-8-carboxylate
Reaktionsgleichung
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:20]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1.O[C:28]1[CH:29]=[CH:30][C:31]2[CH2:37][CH2:36][CH2:35][C:34]([C:38]([O:40][CH3:41])=[O:39])=[CH:33][C:32]=2[CH:42]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[O:20]1[CH2:25][CH2:24][CH:23]([O:26][C:28]2[CH:29]=[CH:30][C:31]3[CH2:37][CH2:36][CH2:35][C:34]([C:38]([O:40][CH3:41])=[O:39])=[CH:33][C:32]=3[CH:42]=2)[CH2:22][CH2:21]1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To triphenylphosphine (1.18 g, 4.50 mmol), tetrahydropyran-4-ol (0.429 g, 4.50 mmol) and methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (327 mg, 1.50 mmol) dissolved in THF (10 ml) was added at 0° C. a solution of diisopropyl azodicarboxylate (0.886 ml, 4.50 mmol) in THF (2 ml), and the resulting mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure and the residue was subjected to column chromatography (silica gel: 45 g, ethyl acetate/hexane=1/25). The objective fractions were concentrated under reduced pressure to obtain methyl 2-[(tetrahydropyran-4-yl)oxy]-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (427 mg, 1.41 mmol, 94%).
Aufarbeitung
- concentrationThe reaction mixture was concentrated under reduced pressure
- concentrationThe objective fractions were concentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-217a2bd3a4524beaad2a8c346da38aa7
- Quelldatensatz
- uspto-grants-2003_09
- Patentnummer
- US06627651B1
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