Iodine → Ethyl 2-iodo-5-phenyl-1,3-oxazole-4-carboxylate

HRID 432090ノート

反応式

HRID 432090 の反応式
[C:1]1([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[I:27]I.CCOC(C)=O>C1COCC1>[I:27][C:10]1[O:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:9]=1

参加物

6

反応物 4

HCID 807IodineHCID 8857Ethyl AcetateHCID 2733832Lithium HexamethyldisilazideHCID 2796947Ethyl 5-phenyl-1,3-oxazole-4-carboxylate

生成物 1

HCID 10268971Ethyl 2-iodo-5-phenyl-1,3-oxazole-4-carboxylate収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of ethyl 5-phenyl-1,3-oxazole-4-carboxylate (Example 29, 0.921 mmol, 1 eq.) in THF (7 mL) at −78° C. was added a solution of lithium bis(trimethylsilyl)amide in THF (1M, 1.11 mmol, 1.2 eq.) dropwise by syringe. The resulting solution was stirred at −78° C. for 1 hour at which time a solution of iodine (1.38 mmol, 1.5 eq. in 2 mL THF) was added dropwise by a syringe. The reaction mixture was allowed to warm to room temperature and stirred at this temperature for 1.5 hours. The resulting solution was poured onto 10% aqueous NaS2O3 (15 mL) and extracted with ethyl acetate. The organic extracts were washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by medium pressure column chromatography (Biotage 40S normal phase silica gel column, hexanes: EtOAc=9:1). The product was obtained as a pale yellow solid in 82% yield. MH+=344.0, Rf=0.31 (hexanes: EtOAc=6:1), retention time (LC-MS)=3.01 min.

後処理

  1. additionwas added dropwise by a syringe
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by medium pressure column chromatography (Biotage 40S normal phase silica gel column, hexanes: EtOAc=9:1)
  7. customThe product was obtained as a pale yellow solid in 82% yield

出典と根拠

ORDレコード
ord-3942963f9c804436ab87c1fc0c0bb314
出典データセット
uspto-grants-2003_12
特許番号
US06660752B2

反応ノート

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