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

HRID 1836959노트

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HRID 1836959 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]([NH-])(C)C.[Li+].[I:23]I.CCOC(C)=O>C1COCC1>[I:23][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 2796947Ethyl 5-phenyl-1,3-oxazole-4-carboxylateHCID 23686461HCID 23686461, 화합물

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 20, 0.921 mmol, 1 eq.) in THF (7 mL) at −78° C. was added a solution of lithium (trimethylsilyl) amide in THF (1 M in THF, 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 rt and stirred at this temperature for 1.5 hours. The resulting solution was poured onto 10% aqueous NaS2O3 (15 mL) and extracted with EtOAc. The organic extracts were washed with brine, dried over anhyd. 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 EtOAc
  3. washThe organic extracts were washed with brine
  4. customdried over anhyd
  5. concentrationsodium sulfate, concentrated 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-145e44e1feb44c32bf0c944bacb22188
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06780859B2

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