Triethylamine → 4-Allyl-4-benzyl-2-phenyl-2-oxazolin-5-one

HRID 366866

反応式

HRID 366866 の反応式
C(O[CH2:5][CH:6]=[CH2:7])(=O)C.C(N(CC)CC)C.CN(C)C(=NC)N(C)C.[CH2:24]([CH:31]1[C:35](=[O:36])[O:34][C:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[CH2:7]([C:31]1([CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:35](=[O:36])[O:34][C:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:32]1)[CH:6]=[CH2:5]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 11584Allyl acetateHCID 139457N,N,N',N',N''-PentamethylguanidineHCID 27566504-Benzyl-2-phenyl-2-oxazolin-5-one

生成物 1

HCID 232902074-Allyl-4-benzyl-2-phenyl-2-oxazolin-5-one

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

Allyl acetate (21.6 μL, 200 μmol) was added to a solution of triethylamine (56 μL, 400 μmol) or pentamethylguanidine (51.7 mg, 400 μmol) and 4-benzyl-2-phenyl-2-oxazolin-5-one (450 μmol) in acetonitrile (1 mL). Then a preformed solution of bis(η3 -allyl)di-,μ-chlorodipalladium (II) (1.8 mg, 4.9 μmol) and ligand 1 (10.4 mg, 15.1 μmol) in acetonitrile (1 mL) was added via cannula. The reaction mixture was quenched with aqueous phosphate buffer (pH 7, 40 ml) and extracted with CH2Cl2 (3×30 mL). The combined organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with petroleum ether-AcOEt (95:5) to give 4-allyl-4-benzyl-2-phenyl-2-oxazolin-5-one. ##STR15##

後処理

  1. customThe reaction mixture was quenched with aqueous phosphate buffer (pH 7, 40 ml)
  2. extractionextracted with CH2Cl2 (3×30 mL)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with petroleum ether-AcOEt (95:5)

出典と根拠

ORDレコード
ord-8effe37986404774ba5a0f798cddf652
出典データセット
uspto-grants-2000_10
特許番号
US06130337

関連ノート

読み込み中…