Benzyl Alcohol → 5-(benzyloxy)-2,3-dihydro-1H-inden-1-one

HRID 507977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507977
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.CCCCCC>[CH2:12]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 244Benzyl AlcoholHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2331475-Hydroxy-1-indanone

Produkt 1

HCID 107524065-(benzyloxy)-2,3-dihydro-1H-inden-1-oneAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 5-hydroxyindan-1-one (1.00 q, 6.17 mmol), benzyl alcohol (800 mg, 7.40 mmol) and tributylphosphine (1.70 g, 8.40 mmol) in tetrahydrofuran (80 mL) was stirred at room temperature, 1,1′-(azodicarbonyl)dipiperidine (2.12 g, 8.40 mmol) was added, and the mixture was stirred for 24 hr. Hexane was added to the reaction mixture, the precipitated insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane) to give the title compound (1.14 g, yield 78%) as pale-yellow crystals.

Aufarbeitung

  1. filtrationthe precipitated insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a18fc6fc942a48f6912acfc6b6752020
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786165B2

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