HCID 72483452, compound → HCID 68448656, compound

HRID 2220575Notes

Reaction equation

HRID 2220575 reaction equation
[CH2:1]([O:3][C:4]1[CH:21]=[CH:20][C:7]2[CH:8]3[CH2:14][CH2:13][CH:12]([CH:15]=[CH:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:22])[CH3:2].[H][H]>C1COCC1.[Pd]>[CH2:1]([O:3][C:4]1[CH:21]=[CH:20][C:7]2[CH:8]3[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:22])[CH3:2]

Participants

5

Reactant 2

HCID 72483452HCID 72483452, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68448656HCID 68448656, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5.1 g (about 10.7 mmol) of (E/Z) isomer mixture of (±)-(3R*, 4aR*, 9bS*)-7-ethoxy-6-fluoro-3-pent-1-enyl-1,2,3,4,4a,9b-hexahydrodibenzofuran in 50 ml of THF are hydrogenated in a hydrogen atmosphere with addition of 5.0 g of Pd/C (5% Pd). After completion of the uptake of hydrogen (37 h), the reaction solution is filtered and concentrated to dryness. The residue is filtered adsorptively (SiO2, toluene), and the beige solid obtained is re-crystallised repeatedly from isopropanol at room temperature, giving (±)-(3R*, 4aR*, 9bS*)-7-ethoxy-6-fluoro-3-pentyl-1,2,3,4,4a,9b-hexahydro-dibenzofuran as colourless solid (melting point 118° C.).

Workup

  1. filtrationAfter completion of the uptake of hydrogen (37 h), the reaction solution is filtered
  2. concentrationconcentrated to dryness
  3. filtrationThe residue is filtered adsorptively (SiO2, toluene)
  4. customthe beige solid obtained
  5. customis re-crystallised repeatedly from isopropanol at room temperature

Sources & evidence

ORD record
ord-829fea35312b4cae98992136e3e4c195
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

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