Methyl iodide → (3S)-3-(4-Hydroxy-phenyl)-hex-4-ynoic acid methyl ester
Reaktionsgleichung
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:13]#[C:14][CH3:15])[CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[CH3:16]I>CC(C)=O>[CH3:16][O:11][C:10](=[O:12])[CH2:9][C@@H:8]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[C:13]#[C:14][CH3:15]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
Phenol 1.4 (23.5 g, 115 mmol) was dissolved in acetone (230 mL) and treated with KHCO3 (11.5 g, 115 mmol). After 15 minutes, methyl iodide (5 mL, 80 mmol) was added, and the reaction stirred at 40° C. for 14 hours. An additional portion of methyl iodide (3 mL, 48 mmol) was added, and heating was continued for 24 hours. Potassium salts were removed by filtration and thoroughly rinsed with acetone. The filtrate was concentrated to an oil which was filtered through a 1 cm plug of silica gel. Elution with 2.5% MeOH in DCM followed by concentration provided phenol 1 (21.5 g) as a light yellow oil. 1H NMR (500 MHz, acetone-d6) δ 8.2 (br s, 1H); 7.20 (d, 2H, J=9.5 Hz); 6.77 (d, 2H, J=9.0 Hz); 3.98 (m, 1H); 3.60 (s, 3H); 2.65 (m, 2H); 1.78 (d, 3H, J=2.5 Hz). MS ESI (pos.) m/e: 219.1 (M+H); 241.1 (M+Na).
Aufarbeitung
- temperatureheating
- waitwas continued for 24 hours
- customPotassium salts were removed by filtration
- washthoroughly rinsed with acetone
- concentrationThe filtrate was concentrated to an oil which
- filtrationwas filtered through a 1 cm plug of silica gel
- washElution with 2.5% MeOH in DCM
- concentrationfollowed by concentration
Quellen und Nachweise
- ORD-Eintrag
- ord-3f246fea1e5f4e3da7c6c771390e33d2
- Quelldatensatz
- uspto-grants-2008_12
- Patentnummer
- US07465804B2
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