Potassium Carbonate → 6-Benzyloxy-benzofuran-2-carboxylic acid tert-butyl ester

HRID 250275

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:24]([O:28][C:29](=[O:32])[CH2:30]Br)([CH3:27])([CH3:26])[CH3:25].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[C:24]([O:28][C:29]([C:30]1[O:17][C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:16]=[CH:15][C:12]=2[CH:13]=1)=[O:32])([CH3:27])([CH3:26])[CH3:25]

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

To a solution of 4-benzyloxy-2-hydroxy-benzaldehyde (5.56 g, 24.4 mmol) in DMF (20 mL) is added K2CO3 (6.73 g, 48.8 mmol), bromo-acetic acid tert-butyl ester (4.75 g, 24.4 mmol), and DBU (1.0 mL). The mixture is heated to 140° C. for 2 hours and cooled to room temperature. The mixture is quenched with water (200 mL) and extracted with EtOAc (100 mL). The organic layer is dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue is purified by silica gel chromatography cluting with 15% EtOAc/Hexanes to provide the title compound (5.68 g, 72%). LC-ES/MS m/e 269.0 (acid, M+1)

Aufarbeitung

temperaturecooled to room temperature
customThe mixture is quenched with water (200 mL)
extractionextracted with EtOAc (100 mL)
dry with materialThe organic layer is dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue is purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-3ecd02b481cc45819b06dbeb464c34e2
Quelldatensatz: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07863302B2

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