Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 3-[2-(4-Benzyloxy-benzoyl)-5-methoxy-phenyl]-1-phenyl-propan-1-one

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Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:16]CCO1.[Li]CCCC.[CH2:28]([O:35][C:36]1[CH:43]=[CH:42][C:39]([C:40]#N)=[CH:38][CH:37]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CC1C=CC(S([O-])(=O)=[O:52])=CC=1.C1C=C[NH+]=CC=1>C1COCC1.CC(C)=O.O>[CH2:28]([O:35][C:36]1[CH:43]=[CH:42][C:39]([C:40]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=2[CH2:10][CH2:11][C:12]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])=[O:52])=[CH:38][CH:37]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

A solution of 2-[2-(2-Bromo-5-methoxy-phenyl)-ethyl]-2-phenyl-[1,3]dioxolane (0.9 g, 2.5 mmol) in 10 ml of dry THF was cooled to −78° C. and n-BuLi (2.5 M in hexane, 1 ml) was added dropwise. The solution was stirred at −78° C. for 2 h and 4-benzyloxy-benzonitrile (0.575 g, 2.75 mmol) in 2 ml of THF was added. The mixture was allowed to warm to room temperature and refluxed overnight. The solution was then quenched with sat. NH4Cl and the solvent was evaporated. A solution of the residue in 20 ml of wet acetone, 5 ml of H2O containing PPTS (188 mg, 0.75 mmol) was refluxed overnight. Regular workup and column purification afforded an unoptimized weight of 0.8 g 3-[2-(4-Benzyloxy-benzoyl)-5-methoxy-phenyl]-1-phenyl-propan-1-one.

Aufarbeitung

temperatureto warm to room temperature
temperaturerefluxed overnight
customThe solution was then quenched with sat. NH4Cl
customthe solvent was evaporated
temperaturewas refluxed overnight
customRegular workup and column purification

Quellen und Nachweise

ORD-Eintrag: ord-67e23a5ea60e4e7686abdd9402568974
Quelldatensatz: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06395911B1

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