HCID 59215267, compound → HCID 59215271, compound

HRID 2244834Notes

Reaction equation

HRID 2244834 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][O:9]2)=[C:4]2[CH:13]=[C:14]([CH:16]3[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]3)[O:15][C:3]=12>C1COCC1.[Pd]>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][O:9]2)=[C:4]2[CH2:13][CH:14]([CH:16]3[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]3)[O:15][C:3]=12

Participants

4

Reactant 1

HCID 59215267HCID 59215267, compound

Product 1

HCID 59215271HCID 59215271, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.00 g (2.99 mmol) of 4,5-difluoro-2-(4-propylcyclohexyl)-8,9-dihydro-7H-furo[3,2-f]chromene is hydrogenated for 15 h at room temperature and atmospheric pressure in THF using elemental hydrogen in the presence of Pd/C (5% Pd). The reaction soln. is concentrated to dryness, and the residue is purified by column chromatography (SiO2, 1-chlorobutane pentane=2:1). Further purification is carried out by recrystallisation from ethanol, giving 4,5-difluoro-2-(4-propylcyclohexyl)-1,7,8,9-tetrahydro-2H-furo[3,2-f]chromene as a colourless solid having an m.p. of 96° C. (Δ∈=−7.0).

Workup

  1. concentrationis concentrated to dryness
  2. customthe residue is purified by column chromatography (SiO2, 1-chlorobutane pentane=2:1)
  3. customFurther purification
  4. customis carried out by recrystallisation from ethanol

Sources & evidence

ORD record
ord-0da8302f9a6447b39fb6365bd44dec3a
Source dataset
uspto-grants-2010_03
Patent number
US07678929B2

Reaction notes

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