Water → HCID 22005233, compound

HRID 1681246Notes

Reaction equation

HRID 1681246 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14](OC)=[O:15])=[C:12]([CH3:18])[N:11]=[C:10]([CH:19]([CH3:21])[CH3:20])[C:9]=2[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:4][CH:3]=1.O>C1(C)C=CC=CC=1.O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([CH2:14][OH:15])=[C:12]([CH3:18])[N:11]=[C:10]([CH:19]([CH3:20])[CH3:21])[C:9]=2[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 10155368HCID 10155368, compound

Product 1

HCID 22005233HCID 22005233, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

26.5 ml (92.75 mmol) of a 3.5 molar solution of sodium bis-(2-methoxyethoxy)-dihydroaluminate in toluene are added under nitrogen to a solution of 9.5 g (26.5 mmol) of the compound from Example 19 in 200 ml of absolute tetrahydrofuran at 0° C. and the mixture is stirred for 30 minutes at room temperature. After cooling again to 0° C., 200 ml of water are cautiously added dropwise and the mixture is extracted three times using 150 ml of ethyl acetate each time. The combined organic phases are washed once with saturated sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo. The residue is chromatographed on a column (200 g of silica gel 70-230 mesh, φ4.5 cm, using ethyl acetate/petroleum ether 2:8).

Workup

  1. temperatureAfter cooling again to 0° C.
  2. extractionthe mixture is extracted three times
  3. washThe combined organic phases are washed once with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on a column (200 g of silica gel 70-230 mesh, φ4.5 cm, using ethyl acetate/petroleum ether 2:8)

Sources & evidence

ORD record
ord-9e12f42415214f3f8f9acab42a21cf13
Source dataset
uspto-grants-1992_12
Patent number
US05169857

Reaction notes

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