N-Methoxy-N-methylbenzamide → 1-Phenyl-3-[3-(4-ethoxybenzyloxy)phenyl]-2-propyne-1-one

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Reaktionsgleichung

C[Si](C)(C)N[Si](C)(C)C.[Li].[CH2:11]([O:13][C:14]1[CH:29]=[CH:28][C:17]([CH2:18][O:19][C:20]2[CH:21]=[C:22]([C:26]#[CH:27])[CH:23]=[CH:24][CH:25]=2)=[CH:16][CH:15]=1)[CH3:12].CON(C)[C:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1>[C:34]1([C:33](=[O:40])[C:27]#[C:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH2:18][C:17]3[CH:28]=[CH:29][C:14]([O:13][CH2:11][CH3:12])=[CH:15][CH:16]=3)[CH:21]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Place lithium hexamethyldisilazane (2 mL of a 1M solution in tetrahydrofuran, 2 mmol) and tetrahydrofuran (8 mL) under an argon atmosphere and cool to 0° C. Add a solution of 3-(4ethoxybenzyloxy)phenylacetylene (0.51 g, 2 mmol) in tetrahydrofuran and stir the solution for 45 minutes at 0° C. Add N-methoxy-N-methylbenzamide (0.4 g, 2.4 mmol), remove the cooling bath andstir at room temperature for 1 hour. Partition the mixture between ethyl ether and water, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo to yield an oil. Filter through silica gel and elute with 10% ethyl acetate/hexane to yield a crude solid. Purifyby silica gel chromatography to give the title compound.

Aufarbeitung

customPartition the mixture between ethyl ether and water
customseparate the organic phase
dry with materialdry (MgSO4)
filtrationFilter
customevaporate the solvent in vacuo
customto yield an oil
filtrationFilter through silica gel
washelute with 10% ethyl acetate/hexane
customto yield a crude solid

Quellen und Nachweise

ORD-Eintrag: ord-937ce94e98ee403e89ed4d1aa1bb21cf
Quelldatensatz: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05446068

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