m-Chloroperbenzoic acid → 4-[4-(methylsulfinyl)phenyl]tetrahydro-2H-pyran-4-carbonitrile
Reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([C:26]#[N:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1>ClCCl>[CH3:12][S:13]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2([C:26]#[N:27])[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)=[CH:18][CH:19]=1)=[O:9]Participants
Procedure
A solution of meta-chloroperbenzoic acid (5.08 g, 22.66 mmol) in dichloromethane (30 ml) was added dropwise over 15 minutes at 0° C. to a solution of 4-[4-(methylthio)phenyl]tetrahydro-2H-pyran-4-carbonitrile (4.8 g, 20.6 mmol) in dichloromethane (40 ml). The reaction mixture was warmed to room temperature over 4 hours. The mixture was then diluted with dichloromethane (180 ml), washed with sodium sulphite solution and 10% aqueous sodium carbonate. The organic layer was separated, dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (100:0:0 to 95:5:0.5 by volume) to provide the title compound (4.55 g, 89%) as an off-white solid. LRMS APCI+ m/z 250 [MH]+.
Workup
- washwashed with sodium sulphite solution and 10% aqueous sodium carbonate
- customThe organic layer was separated
- dry with materialdried over sodium sulphate
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (100:0:0 to 95:5:0.5 by volume)
Sources & evidence
- ORD record
- ord-7497dce5599f498c91b08983297c5383
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07456164B2
Reaction notes
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