Trimethylamine → 2-({[(Prop-2-yn-1-yl)oxy]carbonyl}oxy)ethyl 2-methylprop-2-enoate

HRID 1614022Notes

Reaction equation

HRID 1614022 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][O:7][C:8](=[O:12])[C:9]([CH3:11])=[CH2:10])=[O:3].CN(C)C.[CH2:17]([OH:20])[C:18]#[CH:19]>C(Cl)Cl>[C:8]([O:7][CH2:6][CH2:5][O:4][C:2]([O:20][CH2:17][C:18]#[CH:19])=[O:3])(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 7859Propargyl alcoholHCID 11095475HCID 11095475, compound

Product 1

HCID 199377142-({[(Prop-2-yn-1-yl)oxy]carbonyl}oxy)ethyl 2-methylprop-2-enoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask use in Example 1 was charged with 19.3 g of 2-methacryloyloxyethyl chloroformate and 11.5 g of trimethylamine in 50.0 g of methylene chloride. To the flask was added 7.0 g of propargyl alcohol dropwise over one hour. The mixture was allowed to react for 6 hours at 30° C. After the reaction, the mixture was processed as in Example 1 to give 2-propargyloxycarbonyloxyethyl methacrylate as colorless liquid. Yield, 53.6% of theory. The product was identified to be the same as the product of Example 1 by the IR spectrum and 1H--NMR.

Workup

  1. customto react for 6 hours at 30° C
  2. customAfter the reaction

Sources & evidence

ORD record
ord-8b2538442f5246c0a885b88cd57a05e5
Source dataset
uspto-grants-1993_03
Patent number
US05194655

Reaction notes

Loading…