Dimethylhydantoin → 3-Allyl-5,5-dimethylhydantoin

HRID 1597411

反応式

HRID 1597411 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 5976963-Allyl-5,5-dimethylhydantoin収率 106.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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 title compound.

後処理

  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

出典と根拠

ORDレコード
ord-16810d9117894fc99bebd0a360c69f20
出典データセット
uspto-grants-2001_09
特許番号
US06294573B1

関連ノート

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