4-Chlorophenol → Ethyl 3-(4-benzyloxyphenyl)-2-(4-chlorophenoxy)propionate

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Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:22]S(C)(=O)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31](O)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:22][C:31]2[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

To a solution of ethyl 3-(4-benzyloxyphenyl)-2-methanesulfonyloxypropionate (8.82 g) obtained from Reference example 24(b) and 4-chlorophenol (3.00 g) in N,N-dimethylformamide (110 ml) was added potassium carbonate (6.44 g), and the mixture was stirred at 70° C. for 16 hours. The reaction solution was partitioned between ethyl acetate and water, and then the ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluant; hexane/ethyl acetate=9/1) to afford the target compound (5.99 g) as colorless crystals.

Aufarbeitung

customThe reaction solution was partitioned between ethyl acetate and water
dry with materialthe ethyl acetate layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on a silica gel column (eluant; hexane/ethyl acetate=9/1)

Quellen und Nachweise

ORD-Eintrag: ord-8acfad9080ff47868f007c94862d97a4
Quelldatensatz: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07199139B2

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