Triethylamine → Methyl 2-diphenylphosphino-1-naphthoate

HRID 430040

反応式

HRID 430040 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 11760420Methyl 2-diphenylphosphino-1-naphthoate

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

実験手順

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%

後処理

  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

出典と根拠

ORDレコード
ord-c8bcb54772aa413aa1efe0c4aeaf2465
出典データセット
uspto-grants-2001_11
特許番号
US06320068B1

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