Dimethylhydantoin → 3-Allyl-5,5-dimethylhydantoin

HRID 1978022Notes

Reaction equation

HRID 1978022 reaction equation
[CH2:1](O)[CH2:2][CH:3]=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:25][C:26]1([CH3:33])[NH:30][C:29](=[O:31])[NH:28][C:27]1=[O:32].CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[CH2:3]([N:28]1[C:27](=[O:32])[C:26]([CH3:33])([CH3:25])[NH:30][C:29]1=[O:31])[CH:2]=[CH2:1]

Participants

7

Reactant 4

HCID 6491DimethylhydantoinHCID 11776TriphenylphosphineHCID 693893-Buten-1-olHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 5976963-Allyl-5,5-dimethylhydantoinYield 106.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-buten-1-ol (1 g,13.9 mmol), triphenylphosphine (4.73 g, 18 mmol) and 5,5-dimethylhydantoin (2.1 g, 16.7 mmol) in THF (50 mL) was treated dropwise with diethylazodicarboxylate (3.13 g, 18.0 mmol), stirred at ambient temperature for 1 hour, treated with water, and partitioned between ethyl acetate and brine. The organic layer was dried (Na2SO4), filtered, and concentrated to provide crude product which was purified on silica gel with 50% ethyl acetate/hexanes to provide 2.5 g (100%) of the desired product.

Workup

  1. custompartitioned between ethyl acetate and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide crude product which
  6. customwas purified on silica gel with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1cba829f64924580b4ed6b1c1aa2ebed
Source dataset
uspto-grants-2001_05
Patent number
US06235786B1

Reaction notes

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