Dimethylformamide → HCID 22930724, Verbindung

HRID 2221616

Reaktionsgleichung

Reaktionsgleichung von HRID 2221616
[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[N:7]=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:9][C:10]=1[CH:11]=O.[Cl-].C([O:27][C:28]1[CH:53]=[CH:52][C:31]([CH2:32][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:30][CH:29]=1)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[OH:27][C:28]1[CH:53]=[CH:52][C:31]([CH2:32][CH2:11][C:10]2[O:9][C:8]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[N:7][C:6]=2[CH2:5][O:4][CH2:3][O:2][CH3:1])=[CH:30][CH:29]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 383834[4-(Benzyloxy)benzyl](triphenyl)phosphonium chlorideHCID 114592744-[(Methoxymethoxy)methyl]-2-phenyl-1,3-oxazole-5-carbaldehyde

Produkt 1

HCID 22930724HCID 22930724, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-methoxymethoxymethyl-2-phenyl-1,3-oxazole-5-carbaldehyde (3.00 g), 4-benzyloxybenzyltriphenylphosphonium chloride (6.58 g), potassium carbonate (1.84 g) and N,N-dimethylformamide (50 mL) was stirred at room temperature for 15 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with dilute hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give a colorless oil from a fraction eluted with ethyl acetate-hexane (1:4, v/v). A mixture of the obtained colorless oil, 5% palladium on carbon (5.00 g) and tetrahydrofuran (200 mL) was stirred under a hydrogen atmosphere at room temperature for 3 hrs. After removing palladium on carbon by filtration, the filtrate was concentrated. The obtained crystals were collected by filtration to give 5-[2-(4-hydroxyphenyl)ethyl]-4-methoxymethoxymethyl-2-phenyl-1,3-oxazole (3.24 g, yield 79%). The crystals were recrystallized from ethyl acetate-hexane. melting point: 102-103° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with dilute hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give a colorless oil from a fraction
  6. washeluted with ethyl acetate-hexane (1:4, v/v)
  7. additionA mixture of the obtained colorless oil, 5% palladium on carbon (5.00 g) and tetrahydrofuran (200 mL)
  8. stirringwas stirred under a hydrogen atmosphere at room temperature for 3 hrs
  9. customAfter removing palladium on carbon
  10. filtrationby filtration
  11. concentrationthe filtrate was concentrated
  12. filtrationThe obtained crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-ed9fc8cbe28d4a42af490c6b28ee7a01
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368578B2

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