Methanol → Methyl-4-hydroxy-3-vinylbutyrate

HRID 743844

Reaction equation

HRID 743844 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

HCID 18918398Methyl-4-hydroxy-3-vinylbutyrate

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-70448c2a831c44479f92ea6ac8088e19
Source dataset
uspto-grants-1996_09
Patent number
US05556977

Linked notes

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