Triethylamine → 1-p-Tolyl-3-(t-butyldimethylsiloxy)-2-pyrazoline

HRID 1463077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1463077
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([N:7]2[CH2:11][CH2:10][C:9](=[O:12])[NH:8]2)=[CH:3][CH:2]=1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].C(N(CC)CC)C>C1(C)C=CC=CC=1.O1CCCC1.CN(C1C=CN=CC=1)C.N12CCCN=C1CCCCC2>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([N:7]2[CH2:11][CH2:10][C:9]([O:12][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[N:8]2)=[CH:5][CH:6]=1

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 19134851-(4-Methylphenyl)pyrazolidin-3-one

Produkt 1

HCID 204468861-p-Tolyl-3-(t-butyldimethylsiloxy)-2-pyrazolineAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneKatalysatorHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

To a stirred solution under nitrogen of 1-p-tolyl-3-pyrazolidinone (52.8 g, 0.30 mole) in 500 ml toluene and 50 ml anhydrous tetrahydrofuran was added sequentially t-butyl-dimethylsilyl chloride (49.5 g, 0.30 mole), triethylamine (33.0 g, 0.30 mole), 4-(N,N-dimethylamino)pyridine (0.1 g) and 1,8-diazabicyclo[5.4.0]-undec-7-ene (0.1 g). The mixture was refluxed for 3 hours, then cooled to 30° C., and filtered. After the solids were washed with ether, the solvents of the combined filtrate were removed under reduced pressure. The resulting solid was dissolved in 500 ml anhydrous ether and filtered to remove salts. Removal of the solvent of the filtrate yielded 85.6 g (98% yield) of 1-p-tolyl-3-(t-butyldimethylsiloxy)-2-pyrazoline.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 hours
  2. filtrationfiltered
  3. washAfter the solids were washed with ether
  4. customthe solvents of the combined filtrate were removed under reduced pressure
  5. dissolutionThe resulting solid was dissolved in 500 ml anhydrous ether
  6. filtrationfiltered
  7. customto remove salts
  8. customRemoval of the solvent of the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-10bd69adb4094e7dbaa39dfbe39b9b9d
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04463081

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