Triphenylphosphine → Methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoate

HRID 1251930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1251930
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:21][N:22]1[C:26]([CH2:27][CH:28]([C:30]2[S:31][CH:32]=[CH:33][N:34]=2)O)=[CH:25][N:24]=[CH:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]([O:18][CH:28]([C:30]3[S:31][CH:32]=[CH:33][N:34]=3)[CH2:27][C:26]3[N:22]([CH3:21])[CH:23]=[N:24][CH:25]=3)=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 183244102-(1-Methylimidazol-5-yl)-1-(thiazol-2-yl)ethanolHCID 18324453Methyl 2-(4-fluorophenethyl)-5-hydroxybenzoate

Produkt 1

HCID 18324499Methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoateAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-(4-fluorophenethyl)-5-hydroxybenzoate (1.83 g, 6.7 mmol), 2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethanol (1.40 g, 6.68 mmol) and triphenylphosphine (2.10 g, 8.0 mmol) in tetrahydrofuran (25 ml) was stirred at ambient temperature under a nitrogen atmosphere. DEAD (1.39 g, 1.25 ml 8.0 mmol) was added dropwise to the solution. (The reaction was maintained at ambient temperature ±2° C.). The orange solution was then stirred at ambient temperature under a nitrogen atmosphere for 16 hours. The tetrahydrofiran solution was evaporated to dryness to give an oil. Purification by flash column chromatography eluting with ethyl acetate, ethyl acetate/methanol (9:1 and 4:1) gave methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoate (2.07 g, 67%) as a clear oil.

Aufarbeitung

  1. temperature(The reaction was maintained at ambient temperature ±2° C.)
  2. stirringThe orange solution was then stirred at ambient temperature under a nitrogen atmosphere for 16 hours
  3. customThe tetrahydrofiran solution was evaporated to dryness
  4. customto give an oil
  5. customPurification by flash column chromatography
  6. washeluting with ethyl acetate, ethyl acetate/methanol (9:1 and 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-cd43111c01b94a9795f823b34edf47bb
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06342765B1

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