Ethyl Acetate → HCID 22568824, compound

HRID 2185199Notes

Reaction equation

HRID 2185199 reaction equation
C([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O-:9])=[O:8])=[C:5]([F:12])[C:4]=1O)C.C(C1C=C(C)C=C([C:25]([CH3:28])(C)C)N=1)(C)(C)C.[F:29][C:30]([F:43])([F:42])[S:31]([O:34]S(C(F)(F)F)(=O)=O)(=[O:33])=[O:32].C(OCC)(=O)C>ClCCl.CCCCCC>[CH2:25]([O:9][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([O:34][S:31]([C:30]([F:43])([F:42])[F:29])(=[O:33])=[O:32])=[CH:4][C:5]=1[F:12])[CH3:28]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 67749Trifluoromethanesulfonic anhydrideHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 178436469HCID 178436469, compound2×

Product 1

HCID 22568824HCID 22568824, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A stirred, cooled (ice bath) solution of ethyl-2-fluoro-hydroxy-benzoate (Intermediate 5, 0.368 g, 2 mmol) and 2,6-di-tertbutyl-4-methyl-pyridine (0.81 g, 8 mmol) in 8 mL of dichloromethane was treated with trifluoromethanesulfonic anhydride (0.1 g, 4 mmol). The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was subjected to flash column chromatography over silica gel (230-400 mesh) using 5-10% ethyl acetate in hexane as the eluent to afford the title compound (0.53 g, 85%).

Sources & evidence

ORD record
ord-43448d2e944c4731bef55b93ba5dcf07
Source dataset
uspto-grants-2002_06
Patent number
US06399774B1

Reaction notes

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