Water → HCID 137329061, compound

HRID 1609545Notes

Reaction equation

HRID 1609545 reaction equation
[C:1]([CH:5]([O:30][SiH:31]([CH3:33])[CH3:32])[C:6]1[C:7]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[C:8]([C:18](OCC)=[O:19])[C:9]([CH:15]([CH3:17])[CH3:16])=[N:10][C:11]=1[CH:12]([CH3:14])[CH3:13])([CH3:4])([CH3:3])[CH3:2].O>C1(C)C=CC=CC=1.O1CCCC1>[C:1]([CH:5]([O:30][SiH:31]([CH3:33])[CH3:32])[C:6]1[C:11]([CH:12]([CH3:13])[CH3:14])=[N:10][C:9]([CH:15]([CH3:17])[CH3:16])=[C:8]([CH2:18][OH:19])[C:7]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 148546088HCID 148546088, compound

Product 1

HCID 137329061HCID 137329061, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

9.2 ml (32.2 mmol) of a 3.5 molar solution of sodium bis-(2-methoxyethoxy)-dihydroaluminate in toluene are added under nitrogen to a solution of 4.2 g (9.2 mmol) of the compound from Example 5 in 100 ml of dry tetrahydrofuran at 0° C. and the mixture is stirred overnight at room temperature. After cooling to 0° C., 100 ml of water are cautiously added dropwise and the mixture is extracted three times using 100 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 (100 g of silica gel 70-230 mesh, φ3.5 cm, using ethyl acetate/petroleum ether 2:8).

Workup

  1. temperatureAfter cooling 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 (100 g of silica gel 70-230 mesh, φ3.5 cm, using ethyl acetate/petroleum ether 2:8)

Sources & evidence

ORD record
ord-fce16a4fed344351a705cb560fff10b0
Source dataset
uspto-grants-1995_03
Patent number
US05401746

Reaction notes

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