Triethylamine → Methyl 2-diphenylphosphino-1-naphthoate

HRID 430040

Reaction equation

HRID 430040 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]([O:19][CH3:20])=[O:18])(=O)=O.C(N(CC)CC)C.[C:30]1([PH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:37]1([P:36]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[C:17]([O:19][CH3:20])=[O:18])[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 70017DiphenylphosphineHCID 11034997Methyl 2-trifluoromethanesulfonyloxy-1-naphthoate

Product 1

HCID 11760420Methyl 2-diphenylphosphino-1-naphthoate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A stirred solution of methyl 2-trifluoromethanesulfonyloxy-1-naphthoate (52.7 g, 158 mmol, 1 eq), triethylamine (26.5 ml, 190 mmol, 1.2 eq) and palladium acetate (0.15 g, 0.7 mmol, 0.004 eq) in acetonitrile (600 ml) was sparged with nitrogen for 30 minutes. Diphenylphosphine (29.4 g, 158 mmol, 1 eq) was added instantly giving a red coloration. The solution was heated at reflux under nitrogen for 17 hours. The blood-red solution was allowed to cool and concentrated under reduced pressure to approximately half its original volume. Methanol (50 ml) was added and the mixture concentrated a little more under reduced pressure. The product crystallised from this mixture and was collected by filtration and washed with ice-cold methanol (200 ml) and dried under vacuum at ambient temperature; 31p NMR (162 mHz; CDCl3): δ−7.8. Yield 54.1 g, 92%

Workup

  1. customgiving a red coloration
  2. temperatureThe solution was heated
  3. temperatureat reflux under nitrogen for 17 hours
  4. temperatureto cool
  5. concentrationconcentrated under reduced pressure to approximately half its original volume
  6. additionMethanol (50 ml) was added
  7. concentrationthe mixture concentrated a little more under reduced pressure
  8. customThe product crystallised from this mixture
  9. filtrationwas collected by filtration
  10. washwashed with ice-cold methanol (200 ml)
  11. customdried under vacuum at ambient temperature

Sources & evidence

ORD record
ord-c8bcb54772aa413aa1efe0c4aeaf2465
Source dataset
uspto-grants-2001_11
Patent number
US06320068B1

Linked notes

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