Triethylamine → tert-butyl 4-[2-[(E)-(4-tert-butylphenyl)methylideneamino]oxyethoxy]-2-[4-(trifluoromethyl)benzoyl]oxybenzoate

HRID 29650

Reaktionsgleichung

Reaktionsgleichung von HRID 29650
[C:1]([O:5][C:6](=[O:30])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][O:16][N:17]=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=2)=[CH:9][C:8]=1[OH:29])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:38][C:39]([F:50])([F:49])[C:40]1[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][CH:41]=1>C(Cl)Cl.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:30])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][O:16]/[N:17]=[CH:18]/[C:19]2[CH:20]=[CH:21][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:23][CH:24]=2)=[CH:9][C:8]=1[O:29][C:44](=[O:45])[C:43]1[CH:47]=[CH:48][C:40]([C:39]([F:38])([F:49])[F:50])=[CH:41][CH:42]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 865973854-[2-(4-Tert-butyl-benzylideneaminooxy)-ethoxy]-2-hydroxy-benzoic acid tert-butyl ester

Produkt 1

HCID 87734367tert-butyl 4-[2-[(E)-(4-tert-butylphenyl)methylideneamino]oxyethoxy]-2-[4-(trifluoromethyl)benzoyl]oxybenzoateAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 4-[2-(4-tert-butyl-benzylideneaminooxy)-ethoxy]-2-hydroxy-benzoic acid tert-butyl ester (0.298 g, 0.72 mmol) in methylene chloride (10 mL) was added triethylamine (0.200 mL, 1.43 mmol) and 4-trifluoromethyl benzoyl chloride (0.200 mL, 1.42 mmol). The reaction was stirred at room temperature overnight, poured into brine and the aqueous layer extracted with ethyl acetate. The combined organics dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (8/92) to afford 4-{2-[({(E)-[4-(tert-butyl)phenyl]methylidene}amino)oxy]ethoxy}-2-{[4-(trifluoromethyl)benzoyl]oxy}benzoic acid tert-butyl ester (0.405 g, 96%) as a colorless oil. 1H NMR (300 MHz, CDCl3); δ 8.33 (d, 2H), 8.12 (s, 1H), 7.97 (d, 1H), 7.78 (d, 2H), 7.52 (d, 2H), 7.38 (d, 2H), 6.92 (dd, 1H), 6.76 (d, 1H), 4.50 (t, 2H), 4.33 (t, 2H), 1.40 (s, 9H), 1.30 (s, 9H).

Aufarbeitung

  1. extractionthe aqueous layer extracted with ethyl acetate
  2. dry with materialThe combined organics dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d8ffc7ad244542f48f2c35b36b2adef0
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420083B2

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