Pyridine → 2-Methyl-5-(3-methyloxetan-3-yl)phenyl trifluoromethanesulfonate

HRID 80759Notes

Reaction equation

HRID 80759 reaction equation
[O:1](S(C(F)(F)F)(=O)=O)[S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2([CH3:27])[CH2:26][O:25][CH2:24]2)=[CH:19][C:18]=1O.N1C=CC=CC=1>C(Cl)Cl>[F:6][C:5]([F:8])([F:7])[S:2]([O:1][C:18]1[CH:19]=[C:20]([C:23]2([CH3:27])[CH2:26][O:25][CH2:24]2)[CH:21]=[CH:22][C:17]=1[CH3:16])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86690249HCID 86690249, compound

Product 1

HCID 866902572-Methyl-5-(3-methyloxetan-3-yl)phenyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Tf2O (3.07 mL, 18.2 mmol) was added dropwise to a solution of 2-methyl-5-(3-methyloxetan-3-yl)phenol (2.70 g, 15.2 mmol) and pyridine (1.71 mL, 21.2 mmol) in DCM (25 mL) at 0° C. The red/orange mixture was stirred at 0° C. for 1.5 h, then partitioned between DCM and water. The aqueous layer was extracted with DCM (2×). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography (0-40% EtOAc/heptane) to provide 2-methyl-5-(3-methyloxetan-3-yl)phenyl trifluoromethanesulfonate. 1H NMR (400 MHz, CD2Cl2) δ ppm 7.38 (d, J=8.08 Hz, 1 H) 7.26 (dd, J=7.96, 1.89 Hz, 1 H) 7.14 (d, J=1.77 Hz, 1 H) 4.89 (d, J=5.56 Hz, 2 H) 4.66 (d, J=5.81 Hz, 2 H) 2.41 (s, 3 H) 1.75 (s, 3 H).

Workup

  1. custompartitioned between DCM and water
  2. extractionThe aqueous layer was extracted with DCM (2×)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-40% EtOAc/heptane)

Sources & evidence

ORD record
ord-eef5c18292bb48fcb54e46270ea9e7bf
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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