Allyl Mercaptan → 4-Allylthio-3-ethylazetidinone

HRID 622808Notes

Reaction equation

HRID 622808 reaction equation
[OH-].[Na+].[CH2:3]([SH:6])[CH:4]=[CH2:5].C(O[CH:11]1[NH:14][C:13](=[O:15])[CH:12]1[CH2:16][CH3:17])(=O)C>O>[CH2:3]([S:6][CH:11]1[NH:14][C:13](=[O:15])[CH:12]1[CH2:16][CH3:17])[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 13367Allyl MercaptanHCID 14798Sodium HydroxideHCID 117884382-Azetidinone, 4-(acetyloxy)-3-ethyl-

Product 1

HCID 131064924-Allylthio-3-ethylazetidinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred solution of 3.2 g of sodium hydroxide in 40 ml of water under an argon atmosphere were added 8 ml of allyl thiol (about 85% pure). After 20 minutes of further stirring, a solution of 12.5 g of 4-acetoxy-3-ethylazetidin-2-one in 20 ml of water was added and the mixture was stirred for a further 15 minutes, and then extracted into dichloromethane. The organic extracts were washed with water, were dried over MgSO4, and evaporated in vacuo to dryness. Chromatography over silica gel, eluting with hexane-ethyl acetate mixtures, afforded the title compounds as a yellow oil (3.2 g).

Workup

  1. extractionextracted into dichloromethane
  2. washThe organic extracts were washed with water
  3. dry with materialwere dried over MgSO4
  4. customevaporated in vacuo to dryness
  5. washChromatography over silica gel, eluting with hexane-ethyl acetate mixtures

Sources & evidence

ORD record
ord-7d7798ce1ad0497490737ac0e8c38f60
Source dataset
uspto-grants-1988_09
Patent number
US04772692

Reaction notes

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