Pyridine → 4-(Triethylsilyl)but-3-yn-1-yl 4-methylbenzene-1-sulfonate

HRID 1777558Notes

Reaction equation

HRID 1777558 reaction equation
[CH2:1]([Si:3]([CH2:11][CH3:12])([CH2:9][CH3:10])[C:4]#[C:5][CH2:6][CH2:7][OH:8])[CH3:2].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.N1C=CC=CC=1>ClCCl>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:8][CH2:7][CH2:6][C:5]#[C:4][Si:3]([CH2:1][CH3:2])([CH2:9][CH3:10])[CH2:11][CH3:12])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 27606944-(Triethylsilyl)-3-butyn-1-ol

Product 1

HCID 120301384-(Triethylsilyl)but-3-yn-1-yl 4-methylbenzene-1-sulfonateYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(triethylsilyl)but-3-yn-1-ol (2 mL; 9.22 mmol), p-toluensulfonyl chloride (3.52 g; 18.44 mmol) and pyridine (1.49 mL; 18.44 mmol) in dichloromethane (30 mL) was stirred at room temperature for 3 days. The reaction mixture was then washed with a saturated solution of sodium hydrogen sulphate and brine. The organic layer was dried, concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 3.20 g (quantitative yield) of the desired product as a yellow oil.

Workup

  1. washThe reaction mixture was then washed with a saturated solution of sodium hydrogen sulphate and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customthe crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-13ba07af505747d7b06eb3990a38eda7
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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