Methyl 3-iodobenzoate → Methyl 3-[2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl]benzoate

HRID 399807

Reaktionsgleichung

Reaktionsgleichung von HRID 399807
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[O:13][CH2:14][C:15]([CH3:18])([CH3:17])[N:16]=1)CCC.I[C:28]1[CH:29]=[C:30]([CH:35]=[CH:36][CH:37]=1)[C:31]([O:33][CH3:34])=[O:32].[F-].[K+]>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:18][C:15]1([CH3:17])[CH2:14][O:13][C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:28]2[CH:29]=[C:30]([CH:35]=[CH:36][CH:37]=2)[C:31]([O:33][CH3:34])=[O:32])=[N:16]1

Komponenten

6

Edukt 3

HCID 69258Methyl 3-iodobenzoateHCID 522689Potassium FluorideHCID 189452951-Tri(n-butyl)stannyl-2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)benzene

Produkt 1

HCID 18945305Methyl 3-[2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl]benzoateAusbeute 14,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A suspension of 1-tri(n-butyl)stannyl-2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)benzene (5 g), methyl 3-iodobenzoate (2.17 g) and tetrakis(triphenylphosphine) palladium(0) (0.29 g) in dioxane was refluxed for 18 hours. After being cooled to room temperature, 25% potassium fluoride aqueous solution (11 ml) was added to the reaction mixture and the mixture was stirred for 15 minutes. Insoluble material was filtered by using celite The filtrate was extracted with ethyl acetate (50 ml), washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by column chromatography on silica gel (200 g) with benzene-ethyl acetate (20:1) as an eluent. The fractions containing the object compound were combined and evaporated in vacuo. The residue was recrystallized from methanol to afford methyl 3-[2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl]benzoate (370 mg).

Aufarbeitung

  1. temperaturewas refluxed for 18 hours
  2. filtrationInsoluble material was filtered
  3. extractionwas extracted with ethyl acetate (50 ml)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel (200 g) with benzene-ethyl acetate (20:1) as an eluent
  9. additionThe fractions containing the object compound
  10. customevaporated in vacuo
  11. customThe residue was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-43898460293b4aadbbd077910ed57161
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05824691

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