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

HRID 2244853Notes

Reaction equation

HRID 2244853 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][CH2:15][CH2:16][CH3:17])[O:9]2)=[C:4]2[CH:18]=[C:19]([CH3:21])[O:20][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][CH2:15][CH2:16][CH3:17])[O:9]2)=[C:4]2[CH:18]=[C:19]([CH3:21])[O:20][C:3]=12

Participants

4

Reactant 1

HCID 592152654,5-difluoro-2-methyl-7-pentyl-7H-furo[3,2-f]chromene

Product 1

HCID 592152484,5-difluoro-2-methyl-7-pentyl-8,9-dihydro-7H-furo[3,2-f]chromene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

2.8 g (9.58 mmol) of 4,5-difluoro-2-methyl-7-pentyl-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, giving 4,5-difluoro-2-methyl-7-pentyl-8,9-dihydro-7H-furo[3,2-f]chromene as a colourless solid having an m.p. of 61° C. (Δ∈=−6.7).

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

Sources & evidence

ORD record
ord-1c6ab8fd3fb74505b699a386bf235f5d
Source dataset
uspto-grants-2010_03
Patent number
US07678929B2

Reaction notes

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