Dimethyl Sulfide → 2-Ethoxy-3-(4-hydroxy-benzofuran-7-yl)-propionic acid methyl ester

HRID 479197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479197
CSC.B(F)(F)F.CCOCC.[CH3:13][O:14][C:15](=[O:38])[CH:16]([O:35][CH2:36][CH3:37])[CH2:17][C:18]1[C:26]2[O:25][CH:24]=[CH:23][C:22]=2[C:21]([O:27]CC2C=CC=CC=2)=[CH:20][CH:19]=1>ClCCl>[CH3:13][O:14][C:15](=[O:38])[CH:16]([O:35][CH2:36][CH3:37])[CH2:17][C:18]1[C:26]2[O:25][CH:24]=[CH:23][C:22]=2[C:21]([OH:27])=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 68617324[Rac]-3-(4-benzyloxy-benzofuran-7-yl)-2-ethoxy-propionic acid methyl ester

Produkt 1

HCID 686172122-Ethoxy-3-(4-hydroxy-benzofuran-7-yl)-propionic acid methyl esterAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Dimethyl sulfide (4.4 ml, 60 mmol) and boron trifluoride diethyl etherate (46% purity, 3.3 ml, 12 mmol) were added to a ice cold solution of [rac]-3-(4-benzyloxy-benzofuran-7-yl)-2-ethoxy-propionic acid methyl ester (0.85 g, 2.4 mmol) in dichloromethane (25 ml) under an argon atmosphere. The mixture was stirred for 6 h at ambient temperature, poured into ice water and extracted three times with dichloromethane. The combined extract was washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure gave a brown oil which was purified by column chromatography (silica gel, hexane/AcOEt=4/1) to give 0.45 g (1.7 mmol, 71%) of the title compound as light yellow oil.

Aufarbeitung

  1. extractionextracted three times with dichloromethane
  2. extractionThe combined extract
  3. washwas washed with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent under reduced pressure
  6. customgave a brown oil which
  7. customwas purified by column chromatography (silica gel, hexane/AcOEt=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-cdfa8301c64c4f9593e459fa1c82cb5d
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642389B2

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