Reaktionsgleichung
[H-].[Na+].CN(C=O)C.[C:8]1([OH:21])[C:9]([C:14]2[C:15]([OH:20])=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1.[CH3:22][O:23][CH2:24]Cl.C1[CH2:30][O:29][CH2:28]C1>>[CH3:22][O:23][CH2:24][O:21][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:28][O:29][CH3:30]Komponenten
Versuchsvorschrift
To a 250 mL of three-necked bottle was added NaH (content 50%, 3.5 g, 72 mmol), anhydrous THF (60 mL) and anhydrous DMF (20 mL), after the temperature was lowered to 0° C., a solution of biphenol (5.6 g, 30 mmol) in THF (15 mL) was added, stirred at this temperature for 10 minutes. Methoxymethyl chloride (6 mL, 78 mmol) was added dropwise, and the mixture was stirred for 8 h at room temperature, quenched by adding 100 mL of water, extracted with ethyl acetate (100 mL×3), the combined organic phase was washed with brine (60 mL×2), dried over MgSO4, after filtration, the solvent was removed to give a yellow oil. Purification through chromatography give 8 g (97% yield) of the product as a light yellow oil. 1HNMR (300 MHz, CDCl3) δ (ppm) 3.39 (s, 6H), 5.12 (s, 4H), 7.13 (m, 2H), 7.30–7.37 (m, 6H). Physical data of the compound was consistent with that reported in literature.
Aufarbeitung
- customwas lowered to 0° C.
- stirringthe mixture was stirred for 8 h at room temperature
- customquenched
- additionby adding 100 mL of water
- extractionextracted with ethyl acetate (100 mL×3)
- washthe combined organic phase was washed with brine (60 mL×2)
- dry with materialdried over MgSO4
- filtrationafter filtration
- customthe solvent was removed
- customto give a yellow oil
- customPurification through chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-d4e93b93b1a240b8be74ac423b42f8aa
- Quelldatensatz
- uspto-grants-2006_12
- Patentnummer
- US07151070B2
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