Trifluoromethanesulfonic anhydride → Ethyl 2-(4-(trifluoromethylsulfonyloxy)cyclohex-3-enyl)acetate
Reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.O=[C:32]1[CH2:37][CH2:36][CH:35]([CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:34][CH2:33]1>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:32]1[CH2:37][CH2:36][CH:35]([CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:34][CH:33]=1)(=[O:5])=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Trifluoromethanesulfonic anhydride (11.9 mL, 70.86 mmol) was added portionwise to a solution of 2,6-di-tert-butyl-4-methylpyridine (18.19 g, 88.58 mmol) in DCM (250 mL). A solution of ethyl 2-(4-oxocyclohexyl)acetate (10.88 g, 59.05 mmol, CAS 58012-34-3) in DCM (100 mL) was then added dropwise and the reaction mixture was allowed to stir open to air and at room temperature overnight. The reaction mixture was washed with water, saturated Na2CO3, saturated brine, dried over MgSO4 and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford the title compound (16.05 g, 86%) as a yellow oil.
Workup
- washThe reaction mixture was washed with water, saturated Na2CO3, saturated brine
- dry with materialdried over MgSO4
- customevaporated
- customto afford crude product
- customThe crude product was purified by flash silica chromatography, elution gradient 0 to 10% EtOAc in isohexane
- customPure fractions were evaporated to dryness
Sources & evidence
- ORD record
- ord-8ae7844de8744531828a91ab275af264
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07994179B2
Reaction notes
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