Potassium Carbonate → Methyl 3-(benzyloxy)-5-[4-(methanesulfonyl)phenoxy]benzoate

HRID 20491

Reaktionsgleichung

C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12].F[C:27]1[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1>CN(C=O)C>[C:20]1([CH2:19][O:18][C:16]2[CH:15]=[C:10]([CH:9]=[C:8]([O:7][C:27]3[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

Potassium carbonate (3.21 g, 23.2 mmol) was added to a solution of methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (3.00 g, 11.6 mmol) in DMF (30 mL) followed by addition of 1-fluoro-4-(methylsulfonyl)benzene (2.02 g, 11.6 mmol) and the reaction was heated at 120° C. for 3 h. The solvent was then removed in vacuo and the residue was taken up in saturated aqueous sodium hydrogencarbonate (50 mL) and ethyl acetate (150 mL). The organic layer was separated, washed with 1M aqueous hydrochloric acid (50 mL) then dried (MgSO4), filtered and evaporated. Purification by column chromatography, eluting with 1:4 to 1:1 ethyl acetate:hexanes, afforded the title compound as a colourless oil (3.50 g, 73%).

Aufarbeitung

customThe solvent was then removed in vacuo
customThe organic layer was separated
washwashed with 1M aqueous hydrochloric acid (50 mL)
dry with materialthen dried (MgSO4)
filtrationfiltered
customevaporated
customPurification by column chromatography
washeluting with 1:4 to 1:1 ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-6af20b50dd1745cd86d2fc92c70fc7a5
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07745475B2

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