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

HRID 2175401Notes

Reaction equation

HRID 2175401 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].CCN(CC)CC.[CH3:12][C:13]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])[CH3:14]>C(Cl)Cl>[C:13]([Si:16]([CH3:18])([CH3:17])[O:4][CH2:1][C:2]#[CH:3])([CH3:15])([CH3:14])[CH3:12]

Participants

5

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of prop-2-yn-1-ol (168 g, 3 mol), Et3N (412 g, 4.08 mol) in CH2Cl2 (3500 mL) was added a solution of TBSCl (543 g, 3.45 mol) in CH2Cl2 (500 mL) at 0° C. Then the reaction mixture was warmed up to room temperature and stirred overnight. The mixture was washed by water (3000 mL), dried over Na2SO4, and concentrated to give crude product, which was purified by flash chromatography (petroleum ether) and distillation to give compound S-1 as a yellow liquid. (110 g, 43%)

Workup

  1. washThe mixture was washed by water (3000 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give crude product, which
  5. distillationwas purified by flash chromatography (petroleum ether) and distillation
  6. customto give compound S-1 as a yellow liquid

Sources & evidence

ORD record
ord-d9d43109aafb44c28fc1a0b1f254dc85
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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