Benzaldehyde, 3-(1,1,2,2-tetrafluoroethoxy)- → 3-(3-Phenoxyphenyl)-2-[3-(1,1,2,2-tetrafluoro-ethoxy)phenyl]-5-(trifluoromethyl)oxazolidine

HRID 991330

Reaktionsgleichung

Reaktionsgleichung von HRID 991330
[F:1][C:2]([F:15])([O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11])[CH:3]([F:5])[F:4].[O:16]([C:23]1[CH:24]=[C:25]([NH:29][CH2:30][CH:31](O)[C:32]([F:35])([F:34])[F:33])[CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[Zn+2].[I-].[I-].C1(C)C=CC=CC=1>[O:16]([C:23]1[CH:24]=[C:25]([N:29]2[CH2:30][CH:31]([C:32]([F:33])([F:34])[F:35])[O:11][CH:10]2[C:9]2[CH:12]=[CH:13][CH:14]=[C:7]([O:6][C:2]([F:15])([F:1])[CH:3]([F:4])[F:5])[CH:8]=2)[CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

5

Edukt 2

HCID 118803Benzaldehyde, 3-(1,1,2,2-tetrafluoroethoxy)-HCID 235060633-[(n-3-Phenoxy-phenyl)amino]1,1,1-trifluoro-2-propanol

Produkt 1

HCID 101178453-(3-Phenoxyphenyl)-2-[3-(1,1,2,2-tetrafluoro-ethoxy)phenyl]-5-(trifluoromethyl)oxazolidineAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9883512zinc(II)iodideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A toluene solution (5 mL) of 3-(1,1,2,2-tetrafluoroethoxy)benzaldehyde (0.45 g, 2.0 mol) and N-(3-phenoxyphenyl)-3-amino-1,1,1-trifluoro-2-propanol (0.60 g, 2.0 mmol) was refluxed in the presence of molecular sieves and ZnI2 (˜5 mg) for 18 h under N2. The reaction mixture was filtered to remove the sieves, and the filtrate was diluted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated to give 0.92 g (92%) of the desired 3-(3-phenoxyphenyl)-2-[3-(1,1,2,2-tetrafluoro-ethoxy)phenyl]-5-(trifluoromethyl) oxazolidine product as a colorless oil. The formation of the desired product was monitored by the disappearance of the aldehyde peak (δ10) in the 1H NMR spectrum. HRMS calcd. 502.1253 [M+H]+, found: 502.1220.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customto remove the sieves
  3. additionthe filtrate was diluted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-37ab9ffafd3f46fea18e2925121d83e7
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06462092B1

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