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

HRID 896863노트

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HRID 896863 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-33fc1b72e4f44f428cbdcd3afbffca2e
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919371B2

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