Trimethylsilyl iodide → {3-[5-(4-Ethyl-phenyl)-6-phenyl-pyridin-2-ylmethoxy]-propyl}-phosphonic Acid

HRID 12552

반응식

HRID 12552 반응식
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[CH:22][CH:21]=2)=[C:16]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:15]=1)(=[O:8])[O:5]CC)C.[Si](I)(C)(C)C>C(Cl)(Cl)Cl>[CH2:26]([C:23]1[CH:22]=[CH:21][C:20]([C:17]2[CH:18]=[CH:19][C:14]([CH2:13][O:12][CH2:11][CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5])=[N:15][C:16]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:25][CH:24]=1)[CH3:27]

참가 물질

4

반응물 2

HCID 85247Trimethylsilyl iodideHCID 86619076{3-[5-(4-Ethyl-phenyl)-6-phenyl-pyridin-2-ylmethoxy]-propyl}-phosphonic acid diethyl ester

생성물 1

HCID 44234761{3-[5-(4-Ethyl-phenyl)-6-phenyl-pyridin-2-ylmethoxy]-propyl}-phosphonic Acid

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of crude {3-[5-(4-ethyl-phenyl)-6-phenyl-pyridin-2-ylmethoxy]-propyl}-phosphonic acid diethyl ester (18 mg, 0.039 mmol) in CHCl3 (2 ml) at room temperature was added TMSI (77 mg, 0.39 mmol) dropwise. After the mixture was stirred for 1 hour, the solvent was removed in vacuo to recover a yellow oily residue. The residue was taken-up in THF/H2O (4:1) and stirred at room temperature overnight. The mixture was extracted with ethyl acetate. The combined organic layers were washed with NaHSO3, and water, and brine, and dried over Na2SO4. The filtered solvents were concentrated in vacuo and the residue was purified by MPLC on silica gel (0-100% MeOH in ethyl acetate) to give the title compound as a white solid.

후처리

  1. customthe solvent was removed in vacuo
  2. customto recover a yellow oily residue
  3. stirringstirred at room temperature overnight
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe combined organic layers were washed with NaHSO3, and water, and brine
  6. dry with materialdried over Na2SO4
  7. concentrationThe filtered solvents were concentrated in vacuo
  8. customthe residue was purified by MPLC on silica gel (0-100% MeOH in ethyl acetate)

출처 및 근거

ORD 기록
ord-7e670b67f02e4d5097bc1e3d32aa9157
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728014B2

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