Pyridine → HCID 59168956, compound

HRID 1444800Notes

Reaction equation

HRID 1444800 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[C:5]2[CH3:13].N1C=CC=CC=1.[O:20](S(C(F)(F)F)(=O)=O)[S:21]([C:24]([F:27])([F:26])[F:25])(=O)=[O:22].C(OCC)(=O)C>C(Cl)Cl>[CH3:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([O:1][S:21]([C:24]([F:27])([F:26])[F:25])(=[O:22])=[O:20])[CH:3]=2)[O:8][C:7](=[O:12])[CH:6]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 67749Trifluoromethanesulfonic anhydrideHCID 754096-Hydroxy-4-methyl-2-benzopyrone

Product 1

HCID 59168956HCID 59168956, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6-Hydroxy-4-methyl-chromen-2-one (25 mg, 0.142 mol) and pyridine (300 mL) were dissolved in CH2Cl2 (200 mL) at room temperature and the reaction mixture was cooled to 0° C. and then treated with Tf2O (40 mL). After 1 hour, ethyl acetate (900 mL) was poured into the reaction mixture and the reaction mixture was transferred into a separation funnel. The reaction mixture was then washed with 5% sodium bicarbonate (2×450 ml), water (450 ml) and then brine. The organic layer was dried over sodium sulfate and concentrated. Flash column chromatography on silica gel eluted with 20-50% ethyl acetate in hexane yielded the title compound as a foam.

Workup

  1. customthe reaction mixture was transferred into a separation funnel
  2. washThe reaction mixture was then washed with 5% sodium bicarbonate (2×450 ml), water (450 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. washFlash column chromatography on silica gel eluted with 20-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-cd33b99e1521476390b97d6125b0a0fe
Source dataset
uspto-grants-2010_02
Patent number
US07662975B2

Reaction notes

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