7-Tert-butyl-chroman-4-ol → 7-(Tert-butyl)chroman-4-one

HRID 1879677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879677
[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([OH:15])[CH2:10][CH2:11][O:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:15])[CH2:10][CH2:11][O:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 595485267-Tert-butyl-chroman-4-olHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 595485417-(Tert-butyl)chroman-4-oneAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

7-tert-Butyl-chroman-4-ol (assumed 32.1 mmol) was taken up in dichloromethane (250 mL) and with stirring was added PCC (14.36 g, 2eq) portion-wise. After the addition was complete, the resulting mixture was stirred for about 3 hours by which time the reaction was complete by TLC analysis. About 250 mL of hexanes were added to the mixture and it was then filtered through a pad of celite and the filtrate was concentrated. Purification by column chromatography on silica gel eluting with a gradient of 2% ethyl acetate in hexanes to 10% ethyl acetate in hexanes afforded the title compound as an off-white solid (3.838 g) (M+H)+=205.

Aufarbeitung

  1. additionAfter the addition
  2. stirringthe resulting mixture was stirred for about 3 hours by which time the reaction
  3. filtrationwas then filtered through a pad of celite
  4. concentrationthe filtrate was concentrated
  5. customPurification by column chromatography on silica gel eluting with a gradient of 2% ethyl acetate in hexanes to 10% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f1f36894447f4a57b61a048279b176bb
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318719B2

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