Water → HCID 54136706, compound

HRID 1440983Notes

Reaction equation

HRID 1440983 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](OCC)=[O:23])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[K+]>O1CCCC1>[OH:23][CH2:22][C:9]1[C:10]([CH:19]([CH3:21])[CH3:20])=[N:11][C:12]([CH3:18])=[C:13]([CH2:14][OH:15])[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 10155368HCID 10155368, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 54136706HCID 54136706, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

20.7 g (57.7 mmol) of the compound from Example 26 dissolved in 50 ml of absolute tetrahydrofuran are slowly added dropwise under nitrogen to a suspension of 6 g (158 mmol) of lithium aluminum hydride in 200 ml of absolute tetrahydrofuran at 60° C. The mixture is heated to reflux for 1 h, cooled to 0° C. and 18 ml of water are cautiously added. 6 ml of 10% strength potassium hydroxide solution are added to the mixture, it is filtered off from the precipitate with suction and the residue is boiled twice using 250 ml of ether each time. The combined mother liquors are dried over magnesium sulphate and concentrated in vacuo, The residue is stirred with petroleum ether, filtered off with suction and dried in a desiccator.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 1 h
  3. filtrationis filtered off from the precipitate with suction
  4. dry with materialThe combined mother liquors are dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. filtrationfiltered off with suction
  7. customdried in a desiccator

Sources & evidence

ORD record
ord-2609530195684d0abe5f91e31b0f6633
Source dataset
uspto-grants-1996_03
Patent number
US05502057

Reaction notes

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