(4H,6H,7H-pyrazolo(3,2-c)(1,4)oxazin-2-yl)methanol → 6,7-dihydro-4H-pyrazolo(5,1-c)(1,4)oxazine-2-carbaldehyde

HRID 1158921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158921
[N:1]1[N:9]2[C:4]([CH2:5][O:6][CH2:7][CH2:8]2)=[CH:3][C:2]=1[CH2:10][OH:11]>ClCCCl.[O-2].[O-2].[Mn+4]>[N:1]1[N:9]2[C:4]([CH2:5][O:6][CH2:7][CH2:8]2)=[CH:3][C:2]=1[CH:10]=[O:11]

Komponenten

4

Edukt 1

HCID 11845787(4H,6H,7H-pyrazolo(3,2-c)(1,4)oxazin-2-yl)methanol

Produkt 1

HCID 118454226,7-dihydro-4H-pyrazolo(5,1-c)(1,4)oxazine-2-carbaldehydeAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylmethanol (1.08 g, 7.0 mmol) in 1,2-dichloroethane (30 ml) was added 5.4 g of activated manganese dioxide at room temperature with stirring. The mixture was heated to 60° C. for 1 hr and then stirred at room temperature for 16 hr. The final mixture was filtered through a column of silica gel topped with celite. The filter pad was eluted with methylene chloride, followed by ethyl acetate. The ethyl acetate eluent was evaporated and the residue triturated with to give 0.81 g of a white solid; mp 91° C.; MS (ESI) m/z 153.2 (M+H).

Aufarbeitung

  1. stirringstirred at room temperature for 16 hr
  2. filtrationThe final mixture was filtered through a column of silica gel
  3. washThe filter pad was eluted with methylene chloride
  4. customThe ethyl acetate eluent was evaporated
  5. customthe residue triturated with

Quellen und Nachweise

ORD-Eintrag
ord-1c7c7d3b6dcf4194abfcefb8bc9bb978
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812014B2

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