Allyl Mercaptan → 4-Allylthio-3-ethylazetidinone

HRID 370507Notes

Reaction equation

HRID 370507 reaction equation
[OH-].[Na+].[CH2:3]=[CH:4][CH2:5][SH:6].[CH2:7]([CH:9]1[CH2:12][N:11](OC(=O)C)[C:10]1=[O:17])[CH3:8]>O>[CH2:5]([S:6][CH:12]1[NH:11][C:10](=[O:17])[CH:9]1[CH2:7][CH3:8])[CH:4]=[CH2:3]

Participants

5

Reactant 3

HCID 13367Allyl MercaptanHCID 14798Sodium HydroxideHCID 20275782Ethyl acetoxyazetidinone

Product 1

HCID 131064924-Allylthio-3-ethylazetidinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 1.06 g of sodium hydroxide in 14 ml of water were added 2.82 ml of allylthiol. The solution was stirred under an argon atmosphere for 10 minutes. To this solution was added, over a period of 1 minute, a solution of 3.79 g of ethyl acetoxyazetidinone in 6 ml of water. After about 15 minutes, when the starting material had been consumed, the solution was extracted three times with dichloromethane. The combined organic extracts were back-extracted with water, then dried over magnesium sulphate, evaporated in vacuo, and chromatographed over silica gel, eluting with ethyl acetate/hexane mixtures. The main product (2.84 g) was trans 4-allylthio-3-ethylazetidinone, which contained a trace amount of the cis isomer. (Yield 2.84 g)

Workup

  1. additionTo this solution was added, over a period of 1 minute
  2. waitAfter about 15 minutes
  3. customwhen the starting material had been consumed
  4. extractionthe solution was extracted three times with dichloromethane
  5. extractionThe combined organic extracts were back-extracted with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated in vacuo
  8. customchromatographed over silica gel
  9. washeluting with ethyl acetate/hexane mixtures

Sources & evidence

ORD record
ord-9591f53577ed46d39f65d4f105a421c4
Source dataset
uspto-grants-1985_07
Patent number
US04526718

Reaction notes

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