Trimethylsilylacetylene → HCID 19827489, compound

HRID 1494291Notes

Reaction equation

HRID 1494291 reaction equation
C([Mg]Br)C.[C:5]([Si:7]([CH3:10])([CH3:9])[CH3:8])#[CH:6].[CH3:11][CH:12]([CH3:21])[C:13]([C:15]1[CH:16]=[N:17][CH:18]=[N:19][CH:20]=1)=[O:14]>O1CCCC1>[OH:14][C:13]([C:15]1[CH:20]=[N:19][CH:18]=[N:17][CH:16]=1)([CH:12]([CH3:21])[CH3:11])[C:6]#[C:5][Si:7]([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 13645651HCID 13645651, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 19827489HCID 19827489, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of ethyl magnesium bromide (33 ml of a solution which was 3M in tetrahydrofuran; 0.1 mol) was added to a stirred, cooled solution of ethynyltrimethylsilane (9.8 g,0.1 mol) in dry tetrahydrofuran (150 ml) under nitrogen. The rate of addition was adjusted so as to maintain the reaction temperature below 30° C. After stirring for 45 minutes, 2-methyl-1-pyrimidin-5-ylpropan-1-one (15 g, 0.1 mol) in dry tetrahydrofuran (30 ml) was slowly added. The mixture was allowed to react for 2.8 hours before quenching with dilute aqueous HCl. Extraction with ethyl acetate, drying (over sodium sulphate) and concentration under reduced pressure gave the title compound as white crystals (20.3 g). The product was further purified by recrystallisation from hexane to give a solid of melting point 116.6° C.

Workup

  1. additionThe rate of addition
  2. temperatureto maintain the reaction temperature below 30° C
  3. customto react for 2.8 hours
  4. custombefore quenching with dilute aqueous HCl
  5. extractionExtraction with ethyl acetate
  6. customdrying
  7. concentration(over sodium sulphate) and concentration under reduced pressure

Sources & evidence

ORD record
ord-1ac77c83637b490a8f0831205eb138da
Source dataset
uspto-grants-1991_06
Patent number
US05026418

Reaction notes

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