Hydrochloric Acid → (+/-)-3-(2,4-Dihydroxyphenyl)-1-methylcyclohexanol
Reaktionsgleichung
[CH3:1][Mg]Cl.[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:12]1[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[CH2:13]1.Cl>O1CCCC1>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:12]1[CH2:17][CH2:16][CH2:15][C:14]([CH3:1])([OH:18])[CH2:13]1Komponenten
Versuchsvorschrift
Methyl magnesium chloride (0.132 ml of a 22% w/w solution in tetrahydrofuran) was added to a solution of (±)-3-(2,4-dihydroxyphenyl)cyclohexanone (20 mg) in tetrahydrofuran (3 ml) at 0° C. under argon. After 16 hr, dilute hydrochloric acid (1 ml) was added dropwise and the reaction mixture was partitioned between ethyl acetate (50 ml) and brine (50 ml). The aqueous layer was extracted with ethyl acetate (2×50 ml), and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The crude residue was purified by preparative HPLC to furnish the title compound as a white solid (6 mg, 28%). δH (d4-MeOH) 1.20 (3H, s), 1.22-1.39 (2H, overlapping m), 1.46 (1H, t), 1.54-1.87 (5H, overlapping m), 3.22 (1H, m), 6.19-6.25 (2H, overlapping m), 6.86 91H, d); m/z (ES−) 281 (M+60−H)−.
Aufarbeitung
- customthe reaction mixture was partitioned between ethyl acetate (50 ml) and brine (50 ml)
- extractionThe aqueous layer was extracted with ethyl acetate (2×50 ml)
- dry with materialthe combined organic extracts were dried over magnesium sulfate
- customevaporated in vacuo
- customThe crude residue was purified by preparative HPLC
Quellen und Nachweise
- ORD-Eintrag
- ord-74f247b612f24067917fe9e38c937fc0
- Quelldatensatz
- uspto-grants-2004_12
- Patentnummer
- US06828460B2
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