4,5-difluoro-2-methyl-7-propyl-7H-furo[3,2-f]chromene → 4,5-difluoro-2-methyl-7-propyl-8,9-dihydro-7H-furo[3,2-f]chromene

HRID 2244850Notes

Reaction equation

HRID 2244850 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]([CH2:13][CH2:14][CH3:15])[O:9]2)=[C:4]2[CH:16]=[C:17]([CH3:19])[O:18][C:3]=12>C1(C)C=CC=CC=1.[Pd]>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH3:15])[O:9]2)=[C:4]2[CH:16]=[C:17]([CH3:19])[O:18][C:3]=12

Participants

4

Reactant 1

HCID 592152794,5-difluoro-2-methyl-7-propyl-7H-furo[3,2-f]chromene

Product 1

HCID 592152494,5-difluoro-2-methyl-7-propyl-8,9-dihydro-7H-furo[3,2-f]chromene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

3.5 g (13.2 mmol) of 4,5-difluoro-2-methyl-7-propyl-7H-furo[3,2-f]chromene are hydrogenated for a few minutes in toluene 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, n-heptane:1-chlorobutane=2:1). The further purification is carried out by recrystallisation from ethanol and subsequent absorptive (SiO2, n-heptane:1-chlorobutane=3:1) filtration, giving 4,5-difluoro-2-methyl-7-propyl-8,9-dihydro-7H-furo[3,2-f]chromene as a colourless solid having an m.p. of 75° C. (Δ∈c=−7.8).

Workup

  1. concentrationis concentrated to dryness
  2. customthe residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=2:1)
  3. customThe further purification
  4. customis carried out by recrystallisation from ethanol and subsequent absorptive (SiO2, n-heptane:1-chlorobutane=3:1) filtration

Sources & evidence

ORD record
ord-4b2c6b6166c3485f93372dc13a78e822
Source dataset
uspto-grants-2010_03
Patent number
US07678929B2

Reaction notes

Loading…