Hydrochloric Acid → tert-Butyl(dimethyl)[(prop-2-yn-1-yl)oxy]silane

HRID 1078041Notes

Reaction equation

HRID 1078041 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[CH3:5][C:6]([Si:9](Cl)([CH3:11])[CH3:10])([CH3:8])[CH3:7].N#N.Cl>N1C=CC=CC=1.C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:4][Si:9]([C:6]([CH3:8])([CH3:7])[CH3:5])([CH3:11])[CH3:10])[C:2]#[CH:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 7859Propargyl alcoholHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 3445622tert-Butyl(dimethyl)[(prop-2-yn-1-yl)oxy]silane

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.82 mL of propargyl alcohol in 20 mL of pyridine and 30 mL of CH2Cl2 was added 0.122 g of DMAP and 16.88 g of TBDMSCl in a N2 atmosphere. After stirring 3 days, the reaction was poured into 100 mL of 1N HCl, and diluted with CH2Cl2. The layers were separated and the organic layer washed with 100 mL of 1N HCl (2×), 10% NaHCO3, H2O and brine and dried (MgSO4). Filtration and concentration provided 15.07 g of an oil which was used without purification.

Workup

  1. customThe layers were separated
  2. washthe organic layer washed with 100 mL of 1N HCl (2×), 10% NaHCO3, H2O and brine
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-d0d090ee623f4972aac04475dafc649a
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Reaction notes

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