Acrolein → HCID 18921999, Verbindung

HRID 1289808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1289808
[CH:1]1([C:5]([OH:15])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([OH:8])=[O:7])[CH2:4][CH2:3][CH2:2]1.[CH2:16]1[CH2:26][CH2:25][N:24]2[C:19](=N[CH2:21][CH2:22][CH2:23]2)[CH2:18][CH2:17]1.C(C=C)=O.[I-].[CH:32]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:36]C[CH2:34][CH2:33]1.C([Li])CCC>O1CCCC1.O.CCCCCC>[C:17]1(=[CH:16][CH2:26][CH2:25][N:24]2[CH2:23][CH2:22][CH:21]([O:7][C:6](=[O:8])[C:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)([OH:15])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:18][CH2:19]2)[CH2:34][CH2:33][CH2:32][CH2:36]1

Komponenten

9

Edukt 5

HCID 7847AcroleinHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 108890462-cyclobutyl-2-hydroxy-2-phenylacetic acidHCID 19082503Cyclopentyltriphenylphosphonium iodideHCID 178418339Butyllithium

Produkt 1

HCID 18921999HCID 18921999, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

According to the method of A. Chesnyl et al. [Synthetic Communications, Vol. 20, pp. 3167-3180 (1990)], 50 mg of the 2-cyclobutyl-2-hydroxy-2-phenylacetic acid obtained in Step 1 of Example 1 and a catalytic amount of DBU were dissolved in 2 ml of tetrahydrofuran, and 15 μl of acrolein was added thereto at -15° C., followed by stirring for 20 minutes. The resulting solution was added at 0° C. to an ylide compound prepared from 156 mg of cyclopentyltriphenylphosphonium iodide and 200 μl of n-butyl lithium (as a 1.69M hexane solution), and this mixture was stirred at 0° C. for 30 minutes and then at room temperature for 4 hours. After the addition of 20 ml of water, the reaction mixture was extracted with ethyl acetate (30 ml×3). The organic layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by thin-layer chromatography [Kieselgel™ 60F254, Art 5744 (manufactured by E. Merck); developing solvent: hexane/ethyl acetate=1/2] to obtain 2.0 mg of the title compound.

Aufarbeitung

  1. customat -15° C.
  2. additionThe resulting solution was added at 0° C. to an ylide compound
  3. stirringwas stirred at 0° C. for 30 minutes
  4. waitat room temperature for 4 hours
  5. extractionthe reaction mixture was extracted with ethyl acetate (30 ml×3)
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationAfter the solvent was distilled off under reduced pressure
  9. customthe resulting residue was purified by thin-layer chromatography [Kieselgel™ 60F254, Art 5744 (manufactured by E. Merck); developing solvent: hexane/ethyl acetate=1/2]

Quellen und Nachweise

ORD-Eintrag
ord-f13720c0ff0242cfbadb6b1fd7208e9d
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750540

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