5,6-Difluoro-8-(4-propylcyclohexyl)-1,2,3,8-tetrahydropyrano[3,2-f]chromene → 5,6-Difluoro-3-(4-propylcyclohexyl)-1,2,3,8,9,10-hexahydropyrano[3,2-f]chromene

HRID 1873307Notes

Reaction equation

HRID 1873307 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]([CH:13]3[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]3)[O:9]2)=[C:4]2[CH2:22][CH2:23][CH2:24][O:25][C:3]=12>C1COCC1.[Pd]>[F:12][C:11]1[C:2]([F:1])=[C:3]2[C:4]([CH2:22][CH2:23][CH2:24][O:25]2)=[C:5]2[CH2:6][CH2:7][CH:8]([CH:13]3[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]3)[O:9][C:10]=12

Participants

4

Reactant 1

HCID 581519065,6-Difluoro-8-(4-propylcyclohexyl)-1,2,3,8-tetrahydropyrano[3,2-f]chromene

Product 1

HCID 581519435,6-Difluoro-3-(4-propylcyclohexyl)-1,2,3,8,9,10-hexahydropyrano[3,2-f]chromene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4.0 g (11.5 mmol) of 5,6-difluoro-8-(4-propylcyclohexyl)-1,2,3,8-tetrahydropyrano[3,2-f]chromene are hydrogenated at atmospheric pressure in THF and in the presence of Pd/C (5% of Pd). The reaction solution is filtered, and the filtrate is evaporated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=1:1). The further purification is carried out by repeated recrystallisation from n-heptane at 5° C., giving 5,6-difluoro-3-(4-propylcyclohexyl)-1,2,3,8,9,10-hexahydropyrano[3,2-f]chromene as a colourless solid (m.p. 152° C.).

Workup

  1. filtrationThe reaction solution is filtered
  2. customthe filtrate is evaporated to dryness
  3. customThe residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=1:1)
  4. customThe further purification
  5. customrecrystallisation from n-heptane at 5° C.

Sources & evidence

ORD record
ord-cabba34e4fc24024b91f0bcefd92dac5
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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