Pyridine → 5-Cyclopropyl-2-methylphenyl trifluoromethanesulfonate

HRID 80760Notes

Reaction equation

HRID 80760 reaction equation
N1[CH:6]=[CH:5][CH:4]=CC=1.[O:7](S(C(F)(F)F)(=O)=O)[S:8]([C:11]([F:14])([F:13])[F:12])(=[O:10])=[O:9].CCOC(C)=O.[CH3:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>C(Cl)Cl.[Cl-].[Na+].O>[F:12][C:11]([F:14])([F:13])[S:8]([O:7][C:30]1[CH:31]=[C:32]([CH:4]2[CH2:5][CH2:6]2)[CH:33]=[CH:34][C:29]=1[CH3:28])(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 21899848Ethylacetate heptane

Product 1

HCID 893967175-Cyclopropyl-2-methylphenyl trifluoromethanesulfonate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of the crude product (1.73 g) and pyridine (1.21 mL, 15.0 mmol) in DCM (15 mL), Tf2O (2.17 mL, 12.8 mmol) was added at 0° C. under nitrogen. The mixture was allowed to stir for 1 h. The reaction was monitored by TLC (25% EtOAc/heptane). The mixture was diluted with brine and DCM. The organic layer was separated and concentrated. The residue was purified by flash column chromatography on 40 g silica gel (with 15 g pre-column of silica gel; eluent: heptane/EtOAc=100:0 to 85:15) to give 5-cyclopropyl-2-methylphenyl trifluoromethanesulfonate. 1H NMR (400 MHz, CDCl3) δ ppm 7.16 (d, J=7.87 Hz, 1 H), 6.96 (dd, J=1.64, 7.87 Hz, 1 H), 6.92 (d, J=1.64 Hz, 1 H), 2.32 (s, 3 H), 1.85-1.92 (m, 1 H), 0.97-1.01 (m, 2 H), 0.65-0.69 (m, 2 H).

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated
  3. customThe residue was purified by flash column chromatography on 40 g silica gel (with 15 g pre-column of silica gel; eluent: heptane/EtOAc=100:0 to 85:15)

Sources & evidence

ORD record
ord-60f6812955a5493cad3271e6eb739966
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

Loading…