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

HRID 12552

反応式

HRID 12552 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7e670b67f02e4d5097bc1e3d32aa9157
出典データセット
uspto-grants-2010_06
特許番号
US07728014B2

関連ノート

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