Water → HCID 53719435, compound

HRID 1073109Notes

Reaction equation

HRID 1073109 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([C:10]1[C:15]([C:16](OCC)=[O:17])=[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]([C:27](OCC)=[O:28])=[C:12]([CH:32]([CH3:34])[CH3:33])[N:11]=1)([CH3:9])[CH3:8].O>CCOCC.O1CCCC1>[OH:17][CH2:16][C:15]1[C:10]([CH:7]([CH3:9])[CH3:8])=[N:11][C:12]([CH:32]([CH3:33])[CH3:34])=[C:13]([CH2:27][OH:28])[C:14]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22420887HCID 22420887, compound

Product 1

HCID 53719435HCID 53719435, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

40.5 ml (40.5 mmol) of a 1 molar solution of lithium aluminum hydride in ether are added dropwise under nitrogen to a solution of 6.4 g (16.2 mmol) of the compound from Example 11 in 100 ml of dry tetrahydrofuran at 0° C. The mixture is stirred overnight at room temperature, warmed to 50° C. for 3 h and cooled again to 0° C. 200 ml of water are cautiously added dropwise to the mixture, and it is filtered over kieselguhr with suction and washed with 250 ml of ether. The organic phase is separated, washed once with saturated sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo. The residue is stirred with petroleum ether, and the precipitate is filtered off with suction and dried in a desiccator.

Workup

  1. temperaturewarmed to 50° C. for 3 h
  2. temperaturecooled again to 0° C
  3. filtrationis filtered over kieselguhr with suction
  4. washwashed with 250 ml of ether
  5. customThe organic phase is separated
  6. washwashed once with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated in vacuo
  9. stirringThe residue is stirred with petroleum ether
  10. filtrationthe precipitate is filtered off with suction
  11. customdried in a desiccator

Sources & evidence

ORD record
ord-b80bee46abe34c7eab46b35aadcff297
Source dataset
uspto-grants-1990_11
Patent number
US04968689

Reaction notes

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