Methyl morpholine oxide → Indan-5-carbaldehyde

HRID 1792147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792147
C[N+]1([O-])[CH2:7][CH2:6][O:5]CC1.N1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@H]1C(O)=O>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:11]1[C:12]2[C:17](=[CH:18][C:7]([CH:6]=[O:5])=[CH:14][CH:13]=2)[CH2:16][CH2:15]1

Komponenten

5

Edukt 2

HCID 82029Methyl morpholine oxide2×HCID 2733226(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

Produkt 1

HCID 121624Indan-5-carbaldehydeAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of the alcohol (370 mg, 2.5 mmol) in dichloromethane (10 mL) was stirred at room temperature. N-Methylmorpholine-N-oxide (307 mg, 2.62 mmol) and powdered 4 Å molecular sieves (˜1 g) were added and the mixture was stirred under Ar for 30 minutes. Tetrapropylammonium perruthenate (44 mg, 0.12 mmol) was added in one portion and stirring was continued for 30 minutes. Tic indicated some starting material remaining, so further N-methylmorpholine-N-oxide (100 mg, 0.85 mmol) was added and stirring continued for an additional 30 minutes. The mixture was evaporated onto SiO2 (˜2 g) and purified by flash column chromatography (SiO2, 10% EtOH/Hexane eluent) to afford the aldehyde as a pale yellow oil (299 mg, 82%).

Aufarbeitung

  1. additionwere added
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. stirringstirring
  5. waitcontinued for an additional 30 minutes
  6. customThe mixture was evaporated onto SiO2 (˜2 g)
  7. custompurified by flash column chromatography (SiO2, 10% EtOH/Hexane eluent)

Quellen und Nachweise

ORD-Eintrag
ord-d9fd8deb9f9041d49aa55f11a004bd0c
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074934B2

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