Allyl Mercaptan → 4-Allylthio-3-ethylazetidinone

HRID 1381204Notes

Reaction equation

HRID 1381204 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 compound 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, Chromatography over silica gel
  5. washeluting with hexane-ethyl acetate mixtures

Sources & evidence

ORD record
ord-cd1b454ad4e94b029350ac9c69a3c8bb
Source dataset
uspto-grants-1986_04
Patent number
US04585767

Reaction notes

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