Boron trifluoride etherate → Ethyl 5-oxothiepane-4-carboxylate
Reaction equation
[S:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.B(F)(F)F.[CH3:12]COCC.[N+]([C:22]([O:24][CH2:25][CH3:26])=[O:23])(C([O-])=O)=[N-]>CCOCC>[O:7]=[C:4]1[CH2:5][CH2:6][S:1][CH2:12][CH2:2][CH:3]1[C:22]([O:24][CH2:25][CH3:26])=[O:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
To a cold solution (−30° C.) of tetrahydrothiopyran-4-one (5.0 g, 43.0 mmol) in anhydrous ether, were simultaneously added a solution of boron trifluoride etherate (5.4 ml, 43.0 mmol) in diethyl ether (4.6 ml) and a solution of ethyl diazodicarboxylate (5.8 ml, 55.9 mmol) in diethyl ether (4.6 ml) over 1.5 hours via a syringe pump. Upon completion of additions, the reaction mixture was allowed to stir for an additional hour at −30° C. and then warmed to room temperature. The reaction mixture was washed with 30% potassium carbonate and the organic phase was dried over Na2SO4 and concentrated in vacuo to give ethyl 5-oxothiepane-4-carboxylate as a white solid.
Workup
- temperaturewarmed to room temperature
- washThe reaction mixture was washed with 30% potassium carbonate
- dry with materialthe organic phase was dried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-797dd5e0bf34463b84a44f96f0d53447
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07749994B2
Reaction notes
Loading…