Diethyl Ether → HCID 22731324, Verbindung

HRID 2085578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2085578
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[O:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.[C:15]([Mg]Cl)([CH3:18])([CH3:17])[CH3:16].CCOCC>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:13]([OH:14])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 22731282HCID 22731282, Verbindung2×HCID 178418310HCID 178418310, Verbindung

Produkt 1

HCID 22731324HCID 22731324, VerbindungAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A stirred, cooled (ice-bath) solution of 5-bromo-3,3-dimethyl-2,3-dihydrobenzofuran-7-carbaldehyde (Intermediate 30, 1.72 g, 6.74 mmol) in 15 mL of anhydrous tetrahydrofuran was treated with a 1M solution of tert-butyl magnesium chloride solution in ether (6.74 mL, 6.74 mmol). The reaction mixture was then allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated to an oil that on flash column chromatography using 5% ethyl acetate in hexane as the eluent afforded the title compound (0.95 g, 45%).

Aufarbeitung

  1. washwashed with brine
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated to an oil that on flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5847721867084b0eaa451ab96a20c4d7
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720423B2

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