Triphenylphosphine → ethyl 1-({5-methyl-4-[3-(trifluoromethyl)phenyl]furan-2-yl}methyl)-1H-pyrazole-4-carboxylate

HRID 1257439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257439
[CH3:1][C:2]1[O:6][C:5]([CH2:7]O)=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1.[NH:19]1[CH:23]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:21]=[N:20]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl-].[NH4+]>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([CH2:7][N:19]2[CH:23]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:21]=[N:20]2)=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=1

Komponenten

7

Edukt 5

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 66939730{5-Methyl-4-[3-(trifluoromethyl)phenyl]furan-2-yl}methanol

Produkt 1

HCID 66939161ethyl 1-({5-methyl-4-[3-(trifluoromethyl)phenyl]furan-2-yl}methyl)-1H-pyrazole-4-carboxylateAusbeute 33,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of the compound (0.40 g) obtained in Example 128d, ethyl 1H-pyrazole-4-carboxylate (0.26 g) and triphenylphosphine (0.49 g) in tetrahydrofuran (5 mL) was cooled in an ice bath, diisopropyl azodicarboxylate (0.36 mL) was added, and the mixture was stirred at the same temperature for 1 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane/ethyl acetate) to give the title compound (0.20 g) as a yellow oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-5d7162b648d94ffdbf2c2139c9857ea8
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461348B2

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