Pyridine → 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate

HRID 1897749Notes

Reaction equation

HRID 1897749 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.N1C=CC=CC=1.[O:18](S(C(F)(F)F)(=O)=O)[S:19]([C:22]([F:25])([F:24])[F:23])(=O)=[O:20]>C(Cl)Cl>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:8]=1[O:9][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:20])=[O:18])[CH:2]=[O:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1183VanillinHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 108029624-Formyl-2-methoxyphenyl trifluoromethanesulfonateYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

A stirred solution and cooled (20° C.) solution of 2 (5.0 g, 32.89 mmol) in CH2Cl2 (30 mL) was treated with pyridine (5.2 g, 65.82 mmol). After 15 min, Tf2O (11.13 g, 39.4 mmol) was added dropwise and stirred at −20° C. for 1 h. Reaction mixture was diluted with CH2Cl2 (100 mL). The organic layer was washed with water (50 mL), brine (50 mL) and dried, Solvent was evaporated under reduced pressure and residue purified by column chromatography (Silica gel, 60-120 mesh, hexane:ethyl acetate 93:7) to give 3 (5.7 g, 61%) as a syrup.

Workup

  1. customReaction mixture
  2. washThe organic layer was washed with water (50 mL), brine (50 mL)
  3. customdried
  4. customSolvent was evaporated under reduced pressure and residue
  5. custompurified by column chromatography (Silica gel, 60-120 mesh, hexane:ethyl acetate 93:7)

Sources & evidence

ORD record
ord-f3b24406dd8f4c06b7637d56596c3774
Source dataset
uspto-grants-2013_08
Patent number
US08519154B2

Reaction notes

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