Tributyltin Chloride → HCID 15288193, Verbindung

HRID 362371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362371
[CH3:1][C:2]1([CH3:12])[CH2:6][O:5][C:4]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[N:3]1.C([Li])CCC.C([Sn](Cl)(CCCC)CCCC)CCC.CC1(C)COC(C2SC=CC=2[Sn](CCCC)(CCCC)CCCC)=N1.[N+:57]([C:60]1[CH:67]=[CH:66][CH:65]=[CH:64][C:61]=1[CH2:62]Br)([O-:59])=[O:58]>CCOCC.C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[CH2:6][O:5][C:4]([C:7]2[S:8][CH:9]=[CH:10][C:11]=2[CH2:62][C:61]2[CH:64]=[CH:65][CH:66]=[CH:67][C:60]=2[N+:57]([O-:59])=[O:58])=[N:3]1

Komponenten

9

Edukt 5

HCID 15096Tributyltin ChlorideHCID 77569alpha-Bromo-2-nitrotolueneHCID 50082824,5-dihydro-4,4-dimethyl-2-(2-thienyl)-oxazoleHCID 15288192HCID 15288192, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 15288193HCID 15288193, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 4,5-dihydro-4,4-dimethyl-2-(2-thienyl)-oxazole (4.5 gms 25 mmol) in anhydrous ether at -70° C., n-butyl-lithium (2.5 molar solution in hexane, 11 ml) is added drop by drop under N2 atmosphere. The reaction mixture is stirred at -78° C. for 45 minutes and tri-n-butyltin chloride (8.3 gms 25 mmol) in dry ether is added drop by drop. The reaction mixture is stirred at room temperature for 1 hour and quenched with water. The reaction mixture is extracted with ether, washed well with water, dried and concentrated. The product obtain is pure enough for further transformation. The oil product, 4,5-dihydro-4,4-dimethyl-2-[3-(tributylstannyl)-2-thienyl]-oxazole is mixed with 2-nitrobenzyl bromide (5.5 g 25 mmol) in toluene and refluxed in the presence of tetrakis (triphenylphosphine)-palladium (0) (200 mg) for 16 hours.

Aufarbeitung

  1. stirringThe reaction mixture is stirred at room temperature for 1 hour
  2. customquenched with water
  3. extractionThe reaction mixture is extracted with ether
  4. washwashed well with water
  5. customdried
  6. concentrationconcentrated
  7. customThe product obtain

Quellen und Nachweise

ORD-Eintrag
ord-dd239aaa3f594480b247f768f22cde37
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869483

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