1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Methoxy-4-(pentafluoro-lambda~6~-sulfanyl)benzene
Reaction equation
[F:1][S:2]([F:13])([F:12])([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH2:14]1CCN2C(=NCCC2)CC1>C(=O)(OC)OC.CC(=O)OCC>[CH3:14][O:9][C:6]1[CH:7]=[CH:8][C:3]([S:2]([F:10])([F:11])([F:12])([F:13])[F:1])=[CH:4][CH:5]=1Participants
5
Procedure
5.00 g of 4-pentafluorosulfanylphenol were dissolved in 50.00 g of dimethyl carbonate and 3.46 g of DBU were added. The mixture was boiled under reflux for 10 hours, then allowed to cool and diluted with 200 ml of EA. Subsequently, the mixture was washed twice with 100 ml each time of a 5% aqueous HCl solution, then with 100 ml of a 5% aqueous NaOH solution. Drying was effected over MgSO4 and the solvent was removed under reduced pressure. Chromatography on silica gel using 1:1 DIP/HEP afforded 2.2 g of a colorless oil.
Workup
- temperatureunder reflux for 10 hours
- temperatureto cool
- washSubsequently, the mixture was washed twice with 100 ml each time of a 5% aqueous HCl solution
- customDrying
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-29c9499616b64e1b969a5f1735a778fd
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07317124B2
Reaction notes
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