7-fluoro-2H-chromene → 7-Fluorochroman

HRID 440684Notes

Reaction equation

HRID 440684 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[CH:6]=[CH:7][CH2:8][O:9][C:4]=2[CH:3]=1.[H][H]>[Pd].C(O)C>[F:1][C:2]1[CH:11]=[CH:10][C:5]2[CH2:6][CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 224047387-fluoro-2H-chromeneHCID 178418361HCID 178418361, compound

Product 1

HCID 224048067-FluorochromanYield 85.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 12.1 grams (0.081 mole) of 7-fluoro-2H-1-benzopyran and a catalytic amount of 5% palladium on carbon in about 200 mL of ethanol was shaken in a Parr hydrogenator until the theoretical amount of hydrogen gas was taken up. After this time the reaction mixture was filtered and concentrated under reduced pressure, yielding 10.5 grams of 3,4-dihydro-7-fluoro-2H-1-benzopyran. The NMR spectrum was consistent with the proposed structure.

Workup

  1. filtrationAfter this time the reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-464cc3987a914093b3ef2887855b0806
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

Loading…