Imidazole → 5-(t-Butyldimethylsiloxy)-3-pentyne

HRID 373607Notes

Reaction equation

HRID 373607 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].N1C=CN=[CH:15]1>CN(C=O)C>[O:5]([CH2:1][C:2]#[C:3][CH2:4][CH3:15])[Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 135663-Butyn-1-OLHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 110198575-(t-Butyldimethylsiloxy)-3-pentyne

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-butyn-1-ol (g) (10.0 g) in DMF (80 ml) were added t-butyldimethylsilyl chloride (21.5 g) and imidazol (10.6 g), and the resultant mixture was kept at 35° C. for 7 hours. The reaction mixture was treated in the conventional manner and the obtained crude product was distilled to give the title compound (h).

Workup

  1. additionThe reaction mixture was treated in the conventional manner
  2. customthe obtained crude product
  3. distillationwas distilled

Sources & evidence

ORD record
ord-3085f66b27a34b24b6832478a3b93599
Source dataset
uspto-grants-1992_11
Patent number
US05164415

Reaction notes

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