Water → HCID 73607775, compound

HRID 1736293Notes

Reaction equation

HRID 1736293 reaction equation
[CH2:1]([O:4][C:5]1[CH:20]=[CH:19][C:8]([CH:9]=[CH:10][N+:11](=[N:13][CH:14]([CH3:18])[C:15](=[O:17])[CH3:16])[O-:12])=[CH:7][CH:6]=1)[C:2]#[CH:3].[BH4-].[Na+].O.C(OCC)(=O)C>CN(C)C=O.CO>[CH2:1]([O:4][C:5]1[CH:20]=[CH:19][C:8]([CH:9]=[CH:10][N+:11](=[N:13][CH:14]([CH3:18])[CH:15]([OH:17])[CH3:16])[O-:12])=[CH:7][CH:6]=1)[C:2]#[CH:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 73607789HCID 73607789, compound

Product 1

HCID 73607775HCID 73607775, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

44.39 g (134.4 mmol) of 3-(4-(2-propynyloxy)-styryl-ONN-azoxy)-2,2-propylenedioxybutane, a compound disclosed in EP-A-443,513 was subjected to deketalization reaction with iron chloride-silica gel according to the process disclosed in EP-A-443,513 to give 38.94 g of a crude product of 3-(4-(2-propynyloxy)styryl-ONN-azoxy)-2-butanone as a colorless paste. This was dissolved in a mixed solvent of 80 ml of dimethylformamide and 240 ml of methanol, 5 g (134.4 mmol) of sodium borohydride was added, and the mixture was stirred under ice cooling for 1 hour. After the reaction, 300 ml of water and 200 ml of ethyl acetate were added to the reaction solution to carry out extraction. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (diethyl ether-hexane =2:1) to give 30.75 g of the desired compound as a colorless paste (yield 83%).

Workup

  1. additionwas added
  2. additionwere added to the reaction solution
  3. extractionextraction
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (diethyl ether-hexane =2:1)

Sources & evidence

ORD record
ord-9aee80e33767419cbaa47c8960c9cbb5
Source dataset
uspto-grants-1996_07
Patent number
US05541169

Reaction notes

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