Triphenylphosphine → 5-Ethyl-2-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)-phenoxy]-propyl]furan

HRID 865696

Reaktionsgleichung

Reaktionsgleichung von HRID 865696
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:32]([C:34]1[O:38][C:37]([CH2:39][CH2:40][CH2:41][OH:42])=[CH:36][CH:35]=1)[CH3:33].[CH3:43][N:44]1[N:48]=[N:47][C:46]([C:49]2[CH:54]=[C:53]([CH3:55])[C:52](O)=[C:51]([CH3:57])[CH:50]=2)=[N:45]1>O>[CH2:32]([C:34]1[O:38][C:37]([CH2:39][CH2:40][CH2:41][O:42][C:52]2[C:51]([CH3:57])=[CH:50][C:49]([C:46]3[N:47]=[N:48][N:44]([CH3:43])[N:45]=3)=[CH:54][C:53]=2[CH3:55])=[CH:36][CH:35]=1)[CH3:33]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 148372Win 58768HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 229154015-Ethyl-2-(3-hydroxypropyl)furan2×

Produkt 1

HCID 159546435-Ethyl-2-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)-phenoxy]-propyl]furanAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Diethyl azodicarboxylate (DEAD, 4.84 g; 27.8 mmol) was added under nitrogen to a stirred and cooled (-20° C.) solution of triphenylphosphine (7.37 g; 27.8 mmol), 5-ethyl-2-(3-hydroxypropyl)furan (Intermediate 1c) (3.9 g; 25.3 mmol), and 4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenol (5.69 g; 27.8 mmol). The mixture was stirred at -20° C. for 1/2 h, and then was allowed to warm to room temperature overnight. Water (50 mL) was added to the mixture and the layers were separated. The aqueous layer was extracted with ether (3×50 mL), the organic layer was washed with 10% NaOH solution (3×50 mL), water, and dried over magnesium sulfate. The solvent was concentrated in vacuo to yield a residue and purified by MPLC column chromatography (ethyl acetate/hexane, 3:7) to afford 5.63 g (65%) of 5-ethyl-2-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)-phenoxy]-propyl]furan (Formula II; R3 =5-ethyl, R4 =hydrogen, R1, R2 =3,5-dimethyl, R5 =2-methyltetrazol-5-yl, Y=1,3-propylene).

Aufarbeitung

  1. stirringThe mixture was stirred at -20° C. for 1/2 h
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with ether (3×50 mL)
  4. washthe organic layer was washed with 10% NaOH solution (3×50 mL), water
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solvent was concentrated in vacuo
  7. customto yield a residue
  8. custompurified by MPLC column chromatography (ethyl acetate/hexane, 3:7)

Quellen und Nachweise

ORD-Eintrag
ord-5d747741ff1f4beda690ecf2fbb749f3
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05567717

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