Allyl Alcohol → HCID 18781991, compound

HRID 1420542Notes

Reaction equation

HRID 1420542 reaction equation
[Na].C(O)C=C.[C:6]([S:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])(=O)[CH3:7].C([O:22][CH:23]1[NH:26]C(=O)C1)(=O)C>C(OCC)(=O)C>[CH2:16]([O:15][C:13]([CH2:12][CH2:11][CH2:10][S:9][CH:6]1[NH:26][C:23](=[O:22])[CH2:7]1)=[O:14])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 7858Allyl AlcoholHCID 1199814-Acetoxy-2-azetidinoneHCID 5360545SodiumHCID 18781954HCID 18781954, compound

Product 1

HCID 18781991HCID 18781991, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium (1.15 g) was added to allyl alcohol (50 ml) and this solution treated with allyl 4-(acetylthio)butanoate (10.Og) at room temperature for 20 mins. 4-Acetoxyazetidinone (6.5 g) was added and stirring continued at 20° C. for 1 h The resulting mixture was poured into excess ethyl acetate and the layers separated. The organic layer was washed with water, brine, dried (MgSO4), filtered and evaporated. The residue was chromatographed on silica gel (diethyl ether) to give the title compound as a yellow oil, 5.5 g. 48% yield

Workup

  1. customthe layers separated
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (diethyl ether)

Sources & evidence

ORD record
ord-92e768b62bcd474d93a2b9fc36d38b37
Source dataset
uspto-grants-2000_06
Patent number
US06071899

Reaction notes

Loading…