Tetrahydrofuran → 4-Methoxy-2-(2-methyl-[1,3]-dioxolan-2-yl)benzoxazole-7-carboxylic acid

HRID 275805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275805
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3([CH3:16])[O:15][CH2:14][CH2:13][O:12]3)=[N:7][C:6]=2[C:5]([O:17][CH3:18])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C]=[O:56].[O:57]1[CH2:61]CCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:18][O:17][C:5]1[C:6]2[N:7]=[C:8]([C:11]3([CH3:16])[O:15][CH2:14][CH2:13][O:12]3)[O:9][C:10]=2[C:2]([C:61]([OH:57])=[O:56])=[CH:3][CH:4]=1

Komponenten

8

Edukt 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 183166527-Bromo-4-methoxy-2-(2-methyl-[1,3]-dioxolan-2-yl)benzoxazoleHCID 178418416HCID 178418416, Verbindung

Produkt 1

HCID 183166344-Methoxy-2-(2-methyl-[1,3]-dioxolan-2-yl)benzoxazole-7-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

7-Bromo-4-methoxy-2-(2-methyl-[1,3]-dioxolan-2-yl)benzoxazole (480 mg), palladium acetate (34 mg), 1,3-bis(diphenylphosphino)propane (126 mg), triethylamine (0.21 ml), water (15 ml) and tetrahydrofuran (30 ml) were combined and heated to 90° C. in a Parr apparatus under 1035 kPa (150 psi) of carbon monoxide for 3 days. After cooling to room temperature, the tetrahydrofuran was evaporated in vacuo. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml). The aqueous layer was extracted with ethyl acetate (50 ml). The combined organic extracts were dried over magnesium sulphate, evaporated in vacuo and purified by flash chromatography eluting with ethyl acetate to yield the title compound as a white solid (190 mg).

Aufarbeitung

  1. customthe tetrahydrofuran was evaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate (50 ml) and water (50 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (50 ml)
  4. dry with materialThe combined organic extracts were dried over magnesium sulphate
  5. customevaporated in vacuo
  6. custompurified by flash chromatography
  7. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c26c330d25cb49308191857aa8d3dfd8
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353010B1

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