3,4,5-Trimethoxybenzaldehyde → HCID 11727465, compound

HRID 359929Notes

Reaction equation

HRID 359929 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=[O:7].[C-:15]#[N:16].[K+].[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19]>C(#N)C.[I-].[Zn+2].[I-]>[CH3:14][O:13][C:9]1[CH:8]=[C:5]([CH:6]([O:7][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23])[C:15]#[N:16])[CH:4]=[C:3]([O:2][CH3:1])[C:10]=1[O:11][CH3:12]

Participants

6

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 9032Potassium CyanideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11727465HCID 11727465, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

3,4,5-Trimethoxybenzaldehyde (50 g) is dissolved in acetonitrile (prepared by distillation with phosphorus pentoxide) (250 ml). To this solution are added potassium cyanide (24.9 g), zinc (II) iodide (8.1 g) and tert.-butyldimethylsilyl chloride (46.1 g) and the mixture is stirred at room temperature overnight. Acetonitrile is distilled off from the reaction mixture and to the residue is added diethyl ether and the insoluble materials are filtered off. The filtrate is washed with water, dried and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography [solvent: n-hexane/ethyl acetate (3:1)] and crystallized from a mixture of n-hexane and isopropyl ether to give (3,4,5-trimethoxyphenyl)(tert.-butyldimethylsilyloxy)acetonitrile (67 g) as colorless crystal.

Workup

  1. distillationAcetonitrile is distilled off from the reaction mixture and to the residue
  2. additionis added diethyl ether
  3. filtrationthe insoluble materials are filtered off
  4. washThe filtrate is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography [solvent: n-hexane/ethyl acetate (3:1)]
  8. customcrystallized from a mixture of n-hexane and isopropyl ether

Sources & evidence

ORD record
ord-21c00e4ce99c459e868657577c53c9ea
Source dataset
uspto-grants-1991_03
Patent number
US05003087

Reaction notes

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