Carbon Tetrachloride → Ethyl 3,3-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenoate

HRID 330682

Reaktionsgleichung

Reaktionsgleichung von HRID 330682
C(Cl)(Cl)(Cl)Cl.O1CCCC1.[F:11][C:12]1[CH:26]=[CH:25][C:15]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=O)=[CH:14][CH:13]=1.[CH3:27][N:28]1[C:32]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[N:31][N:30]=[N:29]1>N1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl.O>[F:11][C:12]1[CH:26]=[CH:25][C:15]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:33]([C:32]2[N:28]([CH3:27])[N:29]=[N:30][N:31]=2)[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:14][CH:13]=1

Komponenten

8

Edukt 4

HCID 5943Carbon TetrachlorideHCID 8028TetrahydrofuranHCID 95824,4'-DifluorobenzophenoneHCID 283414Ethyl(1-methyl-1h-tetrazol-5-yl)acetate

Produkt 1

HCID 14539522Ethyl 3,3-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24193Titanium TetrachlorideKatalysatorHCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of titanium tetrachloride (2 mL) and carbon tetrachloride (2 mL) was added to 15 mL of tetrahydrofuran at -78° C. under an argon atmosphere. The suspension was stirred at -78° C. for 30 minutes before 0.2 g of 4,4'-difluorobenzophenone was added. After stirring for an additional 30 minutes, a solution of 0.15 g of ethyl 1-methyl-5-tetrazolylacetate in 1 mL of dry pyridine was added dropwise. The dark brownish suspension was stirred at -78° C. for 15 minutes, then was allowed to warm to 0° C. forming a thick paste. The mixture was allowed to stand for 24 hours at ambient temperature before it was poured into water. The aqueous mixture was extracted with ethyl acetate to yield crude product. Analytical TLC eluted five times with 20% (v/v) ethyl acetate in hexanes showed the desired product at Rf =0.3. Pruification by preparative chromatography on two 20×20 cm 2 0.25 mm TLC plates eluted twice with 20% (v/v) ethyl acetate in hexanes to give the title compound which was identical to the compound of Example 3, Step A.

Aufarbeitung

  1. additionwas added
  2. stirringThe dark brownish suspension was stirred at -78° C. for 15 minutes
  3. customforming a thick paste
  4. waitto stand for 24 hours at ambient temperature before it
  5. extractionThe aqueous mixture was extracted with ethyl acetate
  6. customto yield crude product
  7. washAnalytical TLC eluted five times with 20% (v/v) ethyl acetate in hexanes
  8. washPruification by preparative chromatography on two 20×20 cm 2 0.25 mm TLC plates eluted twice with 20% (v/v) ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b3c777ff545449c0860d8d3fdfc7e356
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04897490

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