Triphenylphosphine → 4-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-ethoxy}-naphthalene-1-carbaldehyde

HRID 479134

Reaktionsgleichung

Reaktionsgleichung von HRID 479134
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][CH2:18][OH:19].O[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH:31]=[O:32])=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:17][CH2:18][O:19][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH:31]=[O:32])=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 3442904-Hydroxy-1-naphthaldehydeHCID 5363146Diisopropyl azodicarboxylateHCID 105881722-(5-Methyl-2-(4-(trifluoromethyl)phenyl)oxazol-4-yl)ethanol

Produkt 1

HCID 180035524-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-ethoxy}-naphthalene-1-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

2.00 g of 2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-ethanol (7.37 mmol) was dissolved in 37 ml of toluene and treated successively at 0° C. with 1.27 g of 4-hydroxy-naphthalene-1-carbaldehyde (7.37 mmol), 1.93 g of triphenylphosphine (7.37 mmol), and 1.49 g (7.37 mmol) of DIAD. The cooling bath was then removed and stirring continued for 2 h. The reaction mixture was then evaporated to dryness in vacuo. Flash chromatography (SiO2, hexane/AcOEt=75/25), followed by boiling up in ether, delivered 1.28 g of the title compound as off-white crystals.

Aufarbeitung

  1. customThe cooling bath was then removed
  2. customThe reaction mixture was then evaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8b747aea718945308ede271b56480a7f
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642389B2

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