Water → tetrahydro-4-(4-iodophenyl)-2H-pyran-4-ol

HRID 230290

반응식

HRID 230290 반응식
C([Li])CCC.I[C:7]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][CH:8]=1.[O:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]1.O>C1COCC1>[I:13][C:10]1[CH:11]=[CH:12][C:7]([C:17]2([OH:20])[CH2:18][CH2:19][O:14][CH2:15][CH2:16]2)=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 12208p-DiiodobenzeneHCID 121599Tetrahydro-4H-pyran-4-oneHCID 178418339Butyllithium

생성물 1

HCID 57033480tetrahydro-4-(4-iodophenyl)-2H-pyran-4-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

Under an argon atmosphere, a solution of n-butyllithium (2.59M, in hexane) (8.76 ml) was added dropwise to a solution of 1,4-diiodobenzene (7.49 g) in anhydrous THF (50 ml) at −78° C., and the resulting mixture was stirred at −78° C. for 30 minutes. Tetrahydro-4H-pyran-4-one (2.09 ml) was added dropwise thereto and the resulting mixture was stirred at −78° C. for 1.5 hours. After stirring the mixture for another 3 hours at room temperature, water was added, and the resulting mixture was extracted with ethyl acetate. Organic layer was washed once with water and once with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was recrystallized from cyclohexane/ethyl acetate mixed solvent to obtain tetrahydro-4-(4-iodophenyl)-2H-pyran-4-ol (4.12 g).

후처리

  1. stirringthe resulting mixture was stirred at −78° C. for 1.5 hours
  2. stirringAfter stirring the mixture for another 3 hours at room temperature
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washOrganic layer was washed once with water and once with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removing anhydrous sodium sulfate
  7. filtrationby filtration
  8. concentrationthe filtrate was concentrated
  9. customThe residue was recrystallized from cyclohexane/ethyl acetate mixed solvent

출처 및 근거

ORD 기록
ord-f166337e7d45420e983bd4ef759d89f5
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566724B2

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