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

HRID 1614021Notes

Reaction equation

HRID 1614021 reaction equation
[C:1]([O:6][CH2:7][CH2:8][OH:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].CN(C)C.Cl[C:15]([O:17][CH2:18][C:19]#[CH:20])=[O:16].C(Cl)Cl.O>C(Cl)Cl>[C:1]([O:6][CH2:7][CH2:8][O:9][C:15]([O:17][CH2:18][C:19]#[CH:20])=[O:16])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 4

HCID 1146TrimethylamineHCID 133602-Hydroxyethyl MethacrylateHCID 3356829Propargyl chloroformateHCID 21908982Water methylene chloride

Product 1

HCID 199377142-({[(Prop-2-yn-1-yl)oxy]carbonyl}oxy)ethyl 2-methylprop-2-enoateYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask equipped with a stirrer, thermometer, nitrogen gas tube and reflux condenser was charged with 13.0 g of 2-hydroxyethyl methacrylate and 11.5 g of trimethylamine in 50.0 g of methylene chloride. To the flask was added 13.0 g of propargyl chloroformate dropwise over one hour. The mixture was allowed to react for 6 hours at 30° C. After the reaction, the mixture was treated with methylene chloride-water mixture. The organic phase was separated and dried over magnesium sulfate. After filtering, the filtrate was evaporated in a rotary evaporator. The resulting residue was applied on a 200 mesh silica gel column and developed with ethyl acetate-hexane mixture. The title compound was obtained as colorless liquid. Yield was 73.6% of theory.

Workup

  1. customA flask equipped with a stirrer
  2. temperaturethermometer, nitrogen gas tube and reflux condenser
  3. customto react for 6 hours at 30° C
  4. customAfter the reaction
  5. customThe organic phase was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtering
  8. customthe filtrate was evaporated in a rotary evaporator

Sources & evidence

ORD record
ord-f2cf3f7058e24c9d8102443bde2ca02d
Source dataset
uspto-grants-1993_03
Patent number
US05194655

Reaction notes

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