HCID 58151924, compound → HCID 58151896, compound

HRID 1873319Notes

Reaction equation

HRID 1873319 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH:9]([CH2:12][CH2:13][CH3:14])[CH:8]=[CH:7][C:6]=2[C:5]2[CH2:15][CH2:16][CH:17]([CH:19]3[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20]3)[CH2:18][C:4]=2[C:3]=1[F:28]>C1COCC1.[Pd]>[F:1][C:2]1[C:11]2[O:10][CH:9]([CH2:12][CH2:13][CH3:14])[CH2:8][CH2:7][C:6]=2[C:5]2[CH2:15][CH2:16][CH:17]([CH:19]3[CH2:20][CH2:21][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:24]3)[CH2:18][C:4]=2[C:3]=1[F:28]

Participants

4

Reactant 1

HCID 58151924HCID 58151924, compound

Product 1

HCID 58151896HCID 58151896, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5.0 g (about 11.4 mmol) of 5,6-difluoro-3-propyl-8-(4-propylcyclohexyl)-7,8,9,10-tetrahydro-3H-benzo[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:toluene=9:1). The further purification is carried out by recrystallisation from ethanol, giving a 1:1 mixture of isomeric 5,6-difluoro-3-propyl-8-(4-propylcyclohexyl)-2,3,7,8,9,10-hexahydro-1H-benzo[f]chromenes (m.p. 89° C.). This can be resolved, for example, by preparative HPLC.

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:toluene=9:1)
  4. customThe further purification
  5. customis carried out by recrystallisation from ethanol
  6. customgiving

Sources & evidence

ORD record
ord-f9294a1812d244c49b360839e10c080d
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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