Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH3:11][C:12]1([CH3:19])[O:16][C@H:15]([CH2:17]O)[CH2:14][O:13]1.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:17][C@@H:15]1[CH2:14][O:13][C:12]([CH3:19])([CH3:11])[O:16]1)[CH:5]=[O:6]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 3-chloro-4-hydroxybenzaldehyde (4.21 g, 27 mmol) in degassed toluene (100 mL) is added ((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (5.35 g, 40.5 mmol), 1,1′-(azodicarbonyl)dipiperidide (13.63 g, 54 mmol) followed by tributylphosphine (10.93 g, 54 mmol). The mixture becomes slightly warm and a precipitate forms. The reaction mixture is diluted with degassed toluene (500 mL) and is stirred at rt for 2 h, then at 60° C. for further 18 h before it is washed with 1 N aq. NaOH (3×150 mL) and water (150 mL). The organic phase is dried over MgSO4, filtered and concentrated to leave a dark brown oil which is chromatographed on silica gel eluting with hexane/EA 4:1 to give the title compound (4.30 g) as yellow oil. 1H NMR (CDC3): δ 9.82 (s, 1H), 7.89 (d, J=1.8 Hz, 1H), 7.74 (dd, J=1.8, 8.2 Hz, 1H), 7.05 (d, J=8.2 Hz, 1H), 4.56-4.43 (m, 1H), 4.23-4.17 (m, 2H), 4.14-4.08 (m, 1H), 4.06-4.00 (m, 1H), 1.47 (s, 3H), 1.41 (s, 3H).
Aufarbeitung
- temperatureThe mixture becomes slightly warm
- washat 60° C. for further 18 h before it is washed with 1 N aq. NaOH (3×150 mL) and water (150 mL)
- dry with materialThe organic phase is dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto leave a dark brown oil which
- customis chromatographed on silica gel eluting with hexane/EA 4:1
Quellen und Nachweise
- ORD-Eintrag
- ord-b579e28e7cbb419cadb7a1b594381961
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08524752B2
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