[2-ethyl-5-(tetrahydro-2H-thiopyran-4-yl)thiophen-3-yl]methanol → 2-ethyl-5-(tetrahydro-2H-thiopyran-4-yl)thiophene-3-carbaldehyde
Reaction equation
[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]Participants
4
Procedure
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.
Workup
- stirringthe mixture was further stirred at room temperature for 5 hr
- filtrationManganese dioxide was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (15% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-e98fec3c85de498c87513c357ae27be0
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309580B2
Reaction notes
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