Pyridine → HCID 57666065, compound

HRID 426308

Reaction equation

HRID 426308 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH3:16][O:17][C:18](=[O:28])[CH2:19][C:20]1[CH:25]=[C:24]([OH:26])[CH:23]=[C:22](O)[CH:21]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:16][O:17][C:18](=[O:28])[CH2:19][C:20]1[CH:25]=[C:24]([O:26][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:8])=[O:6])[CH:23]=[C:22]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])[CH:21]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 579787Methyl 3,5-dihydroxyphenylacetate

Product 1

HCID 57666065HCID 57666065, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Trifluoromethanesulphonic anhydride (7.05 g, 25.0 mmol) was added dropwise to a solution of 3,5-dihydroxyphenyl acetic acid methyl ester (1.80 g, 10.0 mmol) and pyridine (4.9 mL, 60.0 mmol) in DCM (20 mL) at 0° C. The temperature was maintained at 0° C. for 15 mins before warming to room temperature and the mixture stirred for 18 hrs. The reaction was diluted with DCM washed with H2O, Na2CO3, dil. HCl, brine, dried (MgSO4) and evaporated under reduced pressure to give a yellow oil. The residue was purified by flash column chromatography (EtOAc:petroleum ether), yield 4.0 g (89%), 1H NMR (CDCl3) δ 7.31 (d, 2H), 7.17 (t, 1H), 3.74 (s, 3H), 7.73 (s, 2H).

Workup

  1. temperaturebefore warming to room temperature
  2. washwashed with H2O, Na2CO3, dil. HCl, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto give a yellow oil
  6. customThe residue was purified by flash column chromatography (EtOAc:petroleum ether), yield 4.0 g (89%), 1H NMR (CDCl3) δ 7.31 (d, 2H), 7.17 (t, 1H), 3.74 (s, 3H), 7.73 (s, 2H)

Sources & evidence

ORD record
ord-10cdcfd1f2534856853208137ba24cd5
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Linked notes

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