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[2-ethyl-5-(tetrahydro-2H-thiopyran-4-yl)thiophen-3-yl]methanol → 2-ethyl-5-(tetrahydro-2H-thiopyran-4-yl)thiophene-3-carbaldehyde

HRID 1877222
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Reaktionsgleichung

Reaktionsgleichung von HRID 1877222
[CH2:1]([C:3]1[S:4][C:5]([CH:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)=[CH:6][C:7]=1[CH2:8][OH:9])[CH3:2]>O1CCCC1.[O-2].[O-2].[Mn+4]>[CH2:1]([C:3]1[S:4][C:5]([CH:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)=[CH:6][C:7]=1[CH:8]=[O:9])[CH3:2]
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Komponenten

4

Edukt 1

HCID 68512711[2-ethyl-5-(tetrahydro-2H-thiopyran-4-yl)thiophen-3-yl]methanol

Produkt 1

HCID 866463932-ethyl-5-(tetrahydro-2H-thiopyran-4-yl)thiophene-3-carbaldehydeAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysator2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of [2-ethyl-5-(tetrahydro-2H-thiopyran-4-yl)thiophen-3-yl]methanol (2.76 g) synthesized above in tetrahydrofuran (50 mL) was added activated manganese dioxide (15.0 g), and the mixture was stirred at room temperature overnight. Activated manganese dioxide (8.00 g) was added again, and the mixture was further stirred at room temperature for 5 hr. Manganese dioxide was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (15% ethyl acetate/hexane) to give the title compound (1.85 g, 68%) as a colorless oil.

Aufarbeitung

  1. stirringthe mixture was further stirred at room temperature for 5 hr
  2. filtrationManganese dioxide was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (15% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e98fec3c85de498c87513c357ae27be0
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08309580B2

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