Methanol → Methyl-4-hydroxy-3-vinylbutyrate

HRID 864853

Reaktionsgleichung

Reaktionsgleichung von HRID 864853
[CH:1]([CH:3]1[CH2:8][O:7][C:5](=[O:6])[CH2:4]1)=[CH2:2].C([O-])(=O)C.[Na+].[CH3:14][OH:15]>>[OH:15][CH2:14][CH:3]([CH:1]=[CH2:2])[CH2:4][C:5]([O:7][CH3:8])=[O:6]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 517045Sodium AcetateHCID 108662944-vinyl-dihydrofuran-2(3H)-one

Produkt 1

HCID 18918398Methyl-4-hydroxy-3-vinylbutyrate

Versuchsvorschrift

A solution of RS 3-vinylbutyrolactone (3.5 g) and sodium acetate (2.56 g) in methanol (30 ml) was kept for 20 hours. Solvent was evaporated and the residue was partitioned between water and ether. The aqueous layer was extracted twice more with ether and the extracts combined, filtered through phase separating paper and evaporated. The residue was purified by filtration chromatography on silica gel (Merck 7736) starting with 1/9 ethyl acetate/hexane and progressing to 4/6 ethyl acetate/hexane as eluent to give methyl 4-hydroxy-3-vinylbutyrate as an oil; NMR(CDCl3) δ5.73(1H,m), 5.15(2H,m), 3.68(3H,s), 3.60(2H,t), 2.76(1H,m), 2.48(2H,m), 1.69(1H,t); m/e 145(M+H)+.

Aufarbeitung

  1. customSolvent was evaporated
  2. customthe residue was partitioned between water and ether
  3. extractionThe aqueous layer was extracted twice more with ether
  4. filtrationfiltered through phase
  5. customseparating paper
  6. customevaporated
  7. filtrationThe residue was purified by filtration chromatography on silica gel (Merck 7736)

Quellen und Nachweise

ORD-Eintrag
ord-da28a72c631b485db949df59852d8995
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563141

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