Methanol → 5-(2,2-Dimethoxy-ethyl)-2-methyl-thiazole-4-carbonitrile

HRID 1443111Notes

Reaction equation

HRID 1443111 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:9]#[C:10][Si](C)(C)C)=[C:5]([C:7]#[N:8])[N:6]=1.[CH3:15][O-:16].[Na+].[CH3:18][OH:19]>>[CH3:15][O:16][CH:10]([O:19][CH3:18])[CH2:9][C:4]1[S:3][C:2]([CH3:1])=[N:6][C:5]=1[C:7]#[N:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 685385072-Methyl-5-trimethylsilanylethynyl-thiazole-4-carbonitrile

Product 1

HCID 685419275-(2,2-Dimethoxy-ethyl)-2-methyl-thiazole-4-carbonitrile

Procedure

2-Methyl-5-trimethylsilanylethynyl-thiazole-4-carbonitrile (4.56 g, 20.7 mmol) was dissolved in 45 ml methanol and sodium methoxide (5.4N in methanol, 11.5 ml, 62 mmol) was added. The reaction mixture was stirred for 2 hrs at reflux and extracted two times with ethyl acetate and saturated NaHCO3-solution. The organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product (4.5 g, >100%) was used without any further purification for the next step.

Workup

  1. temperatureat reflux
  2. extractionextracted two times with ethyl acetate and saturated NaHCO3-solution
  3. dry with materialThe organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product (4.5 g, >100%) was used without any further purification for the next step

Sources & evidence

ORD record
ord-ac69414ac21c4477976a9ebccf1bc45f
Source dataset
uspto-grants-2010_02
Patent number
US07659401B2

Reaction notes

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