Triethylamine → Propargyl methacrylate silyl protected

HRID 870197Notes

Reaction equation

HRID 870197 reaction equation
[CH3:1][Si:2]([CH2:5][C:6]#[C:7][OH:8])([CH3:4])[CH3:3].CCN(CC)CC.[C:16](Cl)(=[O:20])[C:17]([CH3:19])=[CH2:18]>CCOCC>[CH3:1][Si:2]([CH3:4])([CH3:3])[C:5]#[C:6][CH2:7][O:8][C:16](=[O:20])[C:17]([CH3:19])=[CH2:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 11147726Trimethylsilyl propyn-1-ol

Product 1

HCID 57624376Propargyl methacrylate silyl protected

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of trimethylsilyl propyn-1-ol (1 g, 7.8 mmol) and Et3N (1.4 mL, 10 mmol) in Et2O (10 mL) is cooled to −20° C. and a solution of methacryloyl chloride (0.9 mL, 9.3 mmol) in Et2O (5 mL) is added dropwise over 1 h. The mixture is stirred at this temperature for 30 min, and then allowed to warm to ambient temperature overnight. Any precipitated ammonium salts can be removed by filtration, and volatile components can be removed under reduced pressure. The crude product is then purified by flash chromatography.

Workup

  1. customAny precipitated ammonium salts can be removed by filtration, and volatile components
  2. customcan be removed under reduced pressure
  3. customThe crude product is then purified by flash chromatography

Sources & evidence

ORD record
ord-e05600b893b64e12a60de00003d80127
Source dataset
uspto-grants-2015_03
Patent number
US08969377B2

Reaction notes

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