Tosylmethyl isocyanide → 5-[5-Bromo-3-methoxy-2-(2-trimethylsilanylethoxymethoxy)-phenyl]oxazole

HRID 12295

Reaction equation

HRID 12295 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:19][CH3:20])[C:5]([O:10][CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[C:6]([CH:9]=1)[CH:7]=[O:8].C1(C)C=CC(S([CH2:30][N+:31]#[C-:32])(=O)=O)=CC=1>CO>[Br:1][C:2]1[CH:3]=[C:4]([O:19][CH3:20])[C:5]([O:10][CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:18])[CH3:17])=[C:6]([C:7]2[O:8][CH:32]=[N:31][CH:30]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 161915Tosylmethyl isocyanideHCID 860709695-Bromo-3-methoxy-2-(2-trimethylsilanylethoxymethoxy)benzaldehyde

Product 1

HCID 686811785-[5-Bromo-3-methoxy-2-(2-trimethylsilanylethoxymethoxy)-phenyl]oxazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g of 5-bromo-3-methoxy-2-(2-trimethylsilanylethoxymethoxy)benzaldehyde and 0.54 g of p-toluenesulfonylmethyl isocyanide are dissolved in 40 ml of methanol, 0.38 g of o-potassiumcarbonate is added in portions, and the reaction mixture is heated to reflux for 18 h. The solvent is then distilled off, and the crude product is purified by silica gel chromatography (ethyl acetate/heptane).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 18 h
  3. distillationThe solvent is then distilled off
  4. customthe crude product is purified by silica gel chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-552dac4e3cd44625bf490bacd309abfc
Source dataset
uspto-grants-2010_06
Patent number
US07727989B2

Linked notes

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