HCID 15219973, compound → 1,8-Difluoro-2,7-dioctyloxy-9,10-dihydrophenanthrene

HRID 265212Notes

Reaction equation

HRID 265212 reaction equation
[F:1][C:2]1[C:15]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:11]=3[F:16])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>C1COCC1.[Pd]>[F:1][C:2]1[C:15]2[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:11]=3[F:16])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 1

HCID 15219973HCID 15219973, compound

Product 1

HCID 212673471,8-Difluoro-2,7-dioctyloxy-9,10-dihydrophenanthreneYield 56.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.7 g of 1,8-difluoro-2,7-dioctyloxyphenanthrene in 50 ml of THF hydrogenated at atmospheric pressure at 20° C. with addition of 0.1 g of Pd/C (5% by weight). The catalyst is filtered off, the solvent is removed by vacuum distillation, and the residue is chromatographed on silica gel using dichloromethane. Recrystallization from acetonitrile gives 0.4 g of 1,8-difluoro-2,7-dioctyloxy-9,10-dihydrophenanthrene.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is removed by vacuum distillation
  3. customthe residue is chromatographed on silica gel
  4. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-6e4cb5839b994b2ebe1abb2e18c2d4c0
Source dataset
uspto-grants-1997_07
Patent number
US05648021

Reaction notes

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