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Triethylamine → 7-(4-Fluorophenyl)-7-(1-hydroxy-2-naphthyl)heptanoic acid

HRID 373373
Notes
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Reaction equation

HRID 373373 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([CH:13]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:3]=1.C(N(CC)CC)C>CO.[C].[Pd]>[F:28][C:25]1[CH:24]=[CH:23][C:22]([CH:13]([C:4]2[CH:3]=[CH:2][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[OH:12])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:27][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 145139627-(4-Bromo-1-hydroxy-2-naphthyl)-7-(4-fluorophenyl)heptanoic acid

Product 1

HCID 145139657-(4-Fluorophenyl)-7-(1-hydroxy-2-naphthyl)heptanoic acidYield 66.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7-(4-bromo-1-hydroxy-2-naphthyl)-7-(4-fluorophenyl)heptanoic acid (1.70 g) in methanol (10 ml) were added 5% palladium-carbon (200 mg) and triethylamine (0.53 ml) and hydrogenation was carried out at room temperature for 1.5 hours. The catalyst was filtered off and the filtrate was distilled off at reduced pressure. The residue was extracted by addition of ethyl acetate and water. The ethyl acetate layer was washed with saturated saline and dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by subjecting it to silica gel chromatography and eluting with ethyl acetate/hexane (1:2) to obtain 7-(4-fluorophenyl)-7-(1-hydroxy-2-naphthyl)heptanoic acid (930 mg) (Compound B-3). The physical properties and NMR spectrum data thereof are shown in Table 2.

Workup

  1. filtrationThe catalyst was filtered off
  2. distillationthe filtrate was distilled off at reduced pressure
  3. extractionThe residue was extracted by addition of ethyl acetate and water
  4. washThe ethyl acetate layer was washed with saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified
  8. washeluting with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-9b25ba72802443a1b086186fe2324350
Source dataset
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05162571

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes