Reaktionsgleichung
[C:1](N1C2C(=NC=CC=2)N=N1)(=[O:3])[CH3:2].[CH2:13]([OH:24])[CH2:14][C:15]1[CH:23]=[CH:22][C:20]([OH:21])=[C:17]([O:18][CH3:19])[CH:16]=1.[OH-].[Na+]>C1COCC1.Cl>[C:1]([O:21][C:20]1[CH:22]=[CH:23][C:15]([CH2:14][CH2:13][OH:24])=[CH:16][C:17]=1[O:18][CH3:19])(=[O:3])[CH3:2]Komponenten
Reaktionsbedingungen
- Temperatur
- 25 °C
Versuchsvorschrift
A solution of 1-acetyl-1H-1,2,3-triazolo[4,5-b]pyridine (0.964 g, 5.95 mmol) in dry THF (24 mL) was added to a solution of homovanillyl alcohol (1.00 g, 5.95 mmol) in 1N aq. NaOH (5.95 mL, 5.95 mmol) at 25° C. The reaction was stirred at 25° C. for 60 min. The reaction was diluted with 1N HCl (40 mL) and extracted with Et2O (3×50 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 144 mL, gradient to 50% EtOAc in hexanes over 360 mL, gradient to 100% EtOAc over 1944 mL) to afford 4-(2-hydroxyethyl)-2-methoxyphenyl acetate, as a colorless oil. Rf=0.71 (EtOAc). LCMS calc.=233.1; found=233.1 (M+Na)+. 1H NMR (500 MHz, CDCl3): δ 6.95 (d, J=8.0 Hz, 1 H); 6.83 (d, J=1.8 Hz, 1 H); 6.79 (dd, J=1.8, 8.0 Hz, 1 H); 3.88 (t, J=6.6 Hz, 2 H), 3.84 (s, 3 H); 2.82 (t, J=6.5 Hz, 2 H); 2.30 (s, 3 H); 1.76 (s, 1 H).
Aufarbeitung
- extractionextracted with Et2O (3×50 mL)
- dry with materialThe combined extracts were dried (MgSO4)
- concentrationconcentrated in vacuo
- customto give the crude product
- customThis was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 144 mL, gradient to 50% EtOAc in hexanes over 360 mL, gradient to 100% EtOAc over 1944 mL)
Quellen und Nachweise
- ORD-Eintrag
- ord-c4035f4e93494d4e998e5477266b7216
- Quelldatensatz
- uspto-grants-2013_01
- Patentnummer
- US08354454B2
Verknüpfte Notizen
Wird geladen…