Triethylamine → Methyl 2-diphenylphosphino-1-naphthoate

HRID 430044Notes

Reaction equation

HRID 430044 reaction equation
[C:1]1([PH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)S(O[C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]=1[C:30]([O:32][CH3:33])=[O:31])(=O)=O.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC#N.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:8]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[C:30]([O:32][CH3:33])=[O:31])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 70017DiphenylphosphineHCID 821241,4-Bis(diphenylphosphino)butaneHCID 11034997Methyl 2-trifluoromethanesulfonyloxy-1-naphthoate

Product 1

HCID 11760420Methyl 2-diphenylphosphino-1-naphthoate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

Diphenylphosphine (0.55 mL, 3.16 mmol, 1 eq) was added to a stirred solution of methyl 2-trifluoromethanesulfonyloxy-1-naphthoate (1.047 g, 3.13 mmol, 1 eq), triethylamine (0. 5 mL, 3.59 mmol, 1.1 eq), 1,4-bis(diphenylphosphino)butane (dppb) (0.03 g, 0.07 mmol, 0.02 eq) and palladium acetate (0.005 g, 0.02 mmol, 0.006 eq) in degassed MeCN (10 mL) 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 an aliquot taken for NMR analysis.

Workup

  1. custominstantly giving a red coloration
  2. temperatureThe solution was heated
  3. temperatureat reflux under nitrogen for 17 hours
  4. temperatureto cool

Sources & evidence

ORD record
ord-42d2d7fbc88f4df58c32440cf21ac055
Source dataset
uspto-grants-2001_11
Patent number
US06320068B1

Reaction notes

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